Regioselectivity, Stereoselectivity and Catalysis in Intermolecular Pauson-Khand Reactions: Teaching an Old Dog New Tricks

Sabine Laschat; Armand Becheanu; Thomas Bell; Angelika Baro

doi:10.1055/s-2005-918922

ACCOUNT

Regioselectivity, Stereoselectivity and Catalysis in Intermolecular Pauson-Khand Reactions: Teaching an Old Dog New Tricks

Sabine Laschat*, Armand Becheanu, Thomas Bell, Angelika Baro
Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany
Fax: +49(711)6854285; e-Mail: sabine.laschat@oc.uni-stuttgart.de;

Abstract

Alle Artikel dieser Rubrik

Abstract

Since its discovery in the early seventies the intermolecular Pauson-Khand reaction has made considerable progress towards a powerful synthetic method. This account describes the major accomplishments with respect to reactivity, stereoselectivity and catalytic versions, which have been achieved over the last decade and summarizes mechanistic information being obtained by theoretical and experimental studies.

1 Introduction
2 Reactivity: Improvement by Additives
3 Regioselectivity: Some Mechanistic Struggles
4 Stereoselectivity
4.1 Chiral Precursors
4.2 Chiral Auxiliaries
4.3 Chiral Cobalt Complexes
4.4 Chiral Amine N-Oxides
5 Catalysis
5.1 Cobalt-Catalyzed Reactions
5.2 Ruthenium-Catalyzed Reactions
5.3 Rhodium-Catalyzed Reactions
5.4 Iridium-Catalyzed Reactions
6 Theoretical Studies and some Mechanistic Curiosities
7 Conclusions

Key words

Pauson-Khand reaction - metal-catalysis - stereoselectivity - theoretical studies

Volltext

Referenzen

References

<A NAME="RA38505ST-1">1</A> Pauson PL. Khand IU. Knox GR. Watts WE. J. Chem. Soc. D 1971, 36

Reviews:

<A NAME="RA38505ST-2A">2a</A> Park KH. Chung YK. Synlett 2005, 545

<A NAME="RA38505ST-2B">2b</A> Rodriguez Rivero M. Adrio J. Carretero JC. Synlett 2005, 26

<A NAME="RA38505ST-2C">2c</A> Gibson SE. Mainolfi N. Angew. Chem. Int. Ed. 2005, 44: 3022 ; Angew. Chem. 2005, 117, 3082

<A NAME="RA38505ST-2D">2d</A> Bonaga LVR. Krafft ME. Tetrahedron 2004, 60: 9795

<A NAME="RA38505ST-2E">2e</A> Gibson SE. Stevenazzi A. Angew. Chem. Int. Ed. 2003, 42: 1800 ; Angew. Chem. 2003, 115: 1844

<A NAME="RA38505ST-2F">2f</A> Hanson BE. Comments Inorg. Chem. 2002, 23: 289

<A NAME="RA38505ST-2G">2g</A> Brummond KM. Kent JL. Tetrahedron 2000, 56: 3263

<A NAME="RA38505ST-2H">2h</A> Fletcher AJ. Christie SDR. J. Chem. Soc., Perkin Trans. 1 2000, 1657

<A NAME="RA38505ST-2I">2i</A> Buchwald SL. Hicks FA. In Comprehensive Asymmetric Catalysis Vol. 2: Jacobson EN. Pfaltz A. Yamamoto H. Springer; Berlin: 1999. p.491-510

<A NAME="RA38505ST-2J">2j</A> Chung YK. Coord. Chem. Rev. 1999, 188: 297

<A NAME="RA38505ST-2K">2k</A> Ingate ST. Marco-Contelles J. Org. Prep. Proced. Int. 1998, 30: 121

<A NAME="RA38505ST-2L">2l</A> Geis O. Schmalz H.-G. Angew. Chem. Int. Ed. 1998, 37: 911 ; Angew. Chem. 1998, 110, 955

<A NAME="RA38505ST-2M">2m</A> Jeong N. In Transition Metals in Organic Chemistry Vol. 1: Beller M. Bolm C. Wiley-VCH; Weinheim: 1998. p.560-577

<A NAME="RA38505ST-2N">2n</A> Frühauf H.-W. Chem. Rev. 1997, 97: 523

<A NAME="RA38505ST-2O">2o</A> Schore NE. In Comprehensive Organic Synthesis Vol. 5: Trost BM. Pergamon Press; Oxford: 1991. p.1037-1064

<A NAME="RA38505ST-2P">2p</A> Schore NE. Org. React. 1991, 40: 1

<A NAME="RA38505ST-2Q">2q</A> Pauson PL. Tetrahedron 1985, 41: 5855

<A NAME="RA38505ST-2R">2r</A> Rodriguez Rivero M. Adrio J. Carretero JC. Eur. J. Org. Chem. 2002, 2881

<A NAME="RA38505ST-3">3</A> Magnus P. Principe LM. Tetrahedron Lett. 1985, 26: 4851

<A NAME="RA38505ST-4A">4a</A> Pearson AJ. Dubbert RA. J. Chem. Soc., Chem. Commun. 1991, 202

<A NAME="RA38505ST-4B">4b</A> Pearson AJ. Dubbert RA. Organometallics 1994, 13: 1656

<A NAME="RA38505ST-4C">4c</A> Knölker H.-J. Heber J. Synlett 1993, 924

<A NAME="RA38505ST-4D">4d</A> Pearson AJ. Yao X. Synlett 1997, 1281

<A NAME="RA38505ST-5A">5a</A> Kondo T. Suzuki N. Okada T. Mitsudo T.-A. J. Am. Chem. Soc. 1997, 119: 6187

<A NAME="RA38505ST-5B">5b</A> Morimoto T. Chatani N. Fukumoto Y. Murai S. J. Org. Chem. 1997, 62: 3762

<A NAME="RA38505ST-6A">6a</A> Koga Y. Kobayashi T. Narasaka K. Chem. Lett. 1998, 249

<A NAME="RA38505ST-6B">6b</A> Jeong N. Lee S. Sung BK. Organometallics 1998, 17: 3642

<A NAME="RA38505ST-6C">6c</A> Zhao Z. Ding Y. J. Chem. Soc., Perkin Trans. 1 1998, 171

<A NAME="RA38505ST-7A">7a</A> Pages L. Llebaria A. Camps F. Molins E. Miravitlles C. Moreto JM. J. Am. Chem. Soc. 1992, 114: 10449

<A NAME="RA38505ST-7B">7b</A> Tamao K. Kobayashi K. Ito Y. J. Am. Chem. Soc. 1988, 110: 1286

<A NAME="RA38505ST-7C">7c</A> Tamao K. Kobayashi K. Ito Y. Synlett 1992, 539

<A NAME="RA38505ST-7D">7d</A> Zhang M. Buchwald SL. J. Org. Chem. 1996, 61: 4498

<A NAME="RA38505ST-8">8</A> Jordi L. Segundo A. Camps F. Ricart S. Moreto JM. Organometallics 1993, 12: 3795

<A NAME="RA38505ST-9">9</A> Rutherford DT. Christie SDR. Tetrahedron Lett. 1998, 39: 9805

<A NAME="RA38505ST-10">10</A> Zhao Z. Ding Y. Zhao G. J. Org. Chem. 1998, 63: 9285

<A NAME="RA38505ST-11">11</A> Takahashi T. Xi Z. Nishihara Y. Huo S. Kasai K. Aoyagi K. Denisov V. Negishi E. Tetrahedron 1997, 53: 9123

<A NAME="RA38505ST-12">12</A> Schore NE. Croudace MC. J. Org. Chem. 1981, 46: 5436

<A NAME="RA38505ST-13A">13a</A> Simonian SO. Smit WA. Gybin AS. Shashkov AS. Mikaelian GS. Tarasov VA. Ibragimov II. Caple R. Froen DE. Tetrahedron Lett. 1986, 27: 1245

<A NAME="RA38505ST-13B">13b</A> Shambayati S. Crowe WE. Schreiber SL. Tetrahedron Lett. 1990, 31: 5289

<A NAME="RA38505ST-14">14</A> Krafft ME. Scott IL. Romero RH. Feibelmann S. Van Pelt CE. J. Am. Chem. Soc. 1993, 115: 7199

<A NAME="RA38505ST-15">15</A> Jeong N. Chung YK. Lee BY. Lee SH. Yoo S.-E. Synlett 1991, 204

<A NAME="RA38505ST-16">16</A> Kerr WJ. Lindsay DM. Watson SP. Chem. Commun. 1999, 2551

<A NAME="RA38505ST-17">17</A> Chung YK. Lee BY. Jeong N. Hudecek M. Pauson PL. Organometallics 1993, 12: 220

<A NAME="RA38505ST-18A">18a</A> Sugihara T. Yamada M. Ban H. Yamaguchi M. Kaneko C. Angew. Chem., Int. Ed. Engl. 1997, 36: 2801 ; Angew. Chem. 1997, 109, 2884

<A NAME="RA38505ST-18B">18b</A> Sugihara T. Yamaguchi M. Nishizawa M. Chem.-Eur. J. 2001, 7: 1589

<A NAME="RA38505ST-19">19</A> Krafft ME. Bonaga LVR. Hirosawa C. J. Org. Chem. 2001, 66: 3004

<A NAME="RA38505ST-20">20</A> Sugihara T. Yamada M. Yamaguchi M. Nishizawa M. Synlett 1999, 771

<A NAME="RA38505ST-21">21</A> Kerr WJ. Lindsay DM. McLaughlin M. Pauson PL. Chem. Commun. 2000, 1467

Reviews:

<A NAME="RA38505ST-22A">22a</A> Lindström UM. Chem. Rev. 2002, 102: 2751

<A NAME="RA38505ST-22B">22b</A> Cornils B. Herrmann WA. Aqueous-Phase Organometallic Catalysis: Concepts and Applications Wiley-VCH; Weinheim: 1998.

<A NAME="RA38505ST-22C">22c</A> Li CJ. Chan TH. Organic Reactions in Aqueous Media Wiley; New York: 1997.

<A NAME="RA38505ST-23">23</A> Krafft ME. Wright JA. Bonaga LVR. Tetrahedron Lett. 2003, 44: 3417

<A NAME="RA38505ST-24">24</A> Becheanu A. Laschat S. Synlett 2002, 1865

Reviews:

<A NAME="RA38505ST-25A">25a</A> Sheldon R. Chem. Commun. 2001, 2399

<A NAME="RA38505ST-25B">25b</A> Wasserscheid P. Keim W. Angew. Chem. Int. Ed. 2000, 39: 3772; Angew. Chem. 2000, 112: 3926

<A NAME="RA38505ST-25C">25c</A> Welton T. Chem. Rev. 1999, 99: 2071

<A NAME="RA38505ST-25D">25d</A> Seddon KR. J. Chem. Technol. Biotechnol. 1997, 68: 351

<A NAME="RA38505ST-26">26</A> Muto R. Ogasawara K. Tetrahedron Lett. 2001, 42: 4143

<A NAME="RA38505ST-27A">27a</A> Reichwein JF. Iacono ST. Patel MC. Pagenkopf BL. Tetrahedron Lett. 2002, 43: 3739

<A NAME="RA38505ST-27B">27b</A> Reichwein JF. Iacono ST. Pagenkopf BL. Tetrahedron 2002, 58: 3813

<A NAME="RA38505ST-28A">28a</A> Brummond KM. Sill PC. Rickards B. Geib SJ. Tetrahedron Lett. 2002, 43: 3735

<A NAME="RA38505ST-28B">28b</A> Brummond KM. Sill PC. Chen H. Org. Lett. 2004, 6: 149

<A NAME="RA38505ST-29">29</A> Kerr WJ. McLaughlin M. Pauson PL. Robertson SM. Chem. Commun. 1999, 2171

<A NAME="RA38505ST-30">30</A> de Bruin TJM. Milet A. Greene AE. Gimbert Y. J. Org. Chem. 2004, 69: 1075

<A NAME="RA38505ST-31">31</A> Ahmar M. Chabanis O. Gauthier J. Cazes B. Tetrahedron Lett. 1997, 38: 5277

<A NAME="RA38505ST-32">32</A> Ahmar M. Antras F. Cazes B. Tetrahedron Lett. 1999, 40: 5503

<A NAME="RA38505ST-33A">33a</A> Marchueta I. Verdaguer X. Moyano A. Pericas MA. Riera A. Org. Lett. 2001, 3: 3193

<A NAME="RA38505ST-33B">33b</A> Marchueta I. Olivella S. Sola L. Moyano A. Pericas MA. Riera A. Org. Lett. 2001, 3: 3197

<A NAME="RA38505ST-34">34</A> Khand IU. Pauson PL. J. Chem. Res., Synop. 1977, 9

<A NAME="RA38505ST-35A">35a</A> MacWhorter SE. Sampath V. Olmstead MM. Schore NE. J. Org. Chem. 1988, 53: 203

<A NAME="RA38505ST-35B">35b</A> Schore NE. Najdi SD. J. Am. Chem. Soc. 1990, 112: 441

<A NAME="RA38505ST-35C">35c</A> Price ME. Schore NE. J. Org. Chem. 1989, 54: 5662

<A NAME="RA38505ST-35D">35d</A> Price ME. Schore NE. Tetrahedron Lett. 1989, 30: 5865

<A NAME="RA38505ST-35E">35e</A> La Belle BE. Knudsen MJ. Olmstead MM. Hope H. Yanuck MD. Schore NE. J. Org. Chem. 1985, 50: 5215

<A NAME="RA38505ST-36">36</A> Schore NE. In Comprehensive Organometallic Chemistry II Vol. 12: Abel EW. Stone FGA. Wilkinson G. Pergamon Press; Oxford: 1995. p.703-739

<A NAME="RA38505ST-37">37</A> Derdau V. Laschat S. Jones PG. Eur. J. Org. Chem. 2000, 681

<A NAME="RA38505ST-38">38</A> Ahmar M. Cazes B. Tetrahedron Lett. 2003, 44: 5403

<A NAME="RA38505ST-39A">39a</A> Arjona O. Csaky AG. Murcia MC. Plumet J. J. Org. Chem. 1999, 64: 7338

<A NAME="RA38505ST-39B">39b</A> Arjona O. Csaky AG. Medel R. Plumet J. Tetrahedron Lett. 2001, 42: 3085

<A NAME="RA38505ST-40">40</A> Mayo P. Tam W. Tetrahedron 2001, 57: 5943

<A NAME="RA38505ST-41">41</A> Ahmar M. Chabanis O. Gauthier J. Cazes B. Tetrahedron Lett. 1997, 38: 5277

<A NAME="RA38505ST-42">42</A> Antras F. Ahmar M. Cazes B. Tetrahedron Lett. 2001, 42: 8153

<A NAME="RA38505ST-43">43</A> Kerr WJ. McLaughlin M. Pauson PL. Robertson SM. J. Organomet. Chem. 2001, 630: 104

<A NAME="RA38505ST-44">44</A> de Bruin TJM. Milet A. Robert F. Gimbert Y. Greene AE. J. Am. Chem. Soc. 2001, 123: 7184

<A NAME="RA38505ST-45">45</A> Robert F. Milet A. Gimbert Y. Konya D. Greene AE. J. Am. Chem. Soc. 2001, 123: 5396

<A NAME="RA38505ST-46">46</A> Marco-Contelles J. Ruiz J. Tetrahedron Lett. 1998, 39: 6393

<A NAME="RA38505ST-47">47</A> Grossman RB. Tetrahedron 1999, 55: 919

<A NAME="RA38505ST-48A">48a</A> Rivero MR. de la Rosa JC. Carretero JC. J. Am. Chem. Soc. 2003, 125: 14992

<A NAME="RA38505ST-48B">48b</A> Rivero MR. Alonso I. Carretero JC. Chem.-Eur. J. 2004, 10: 5443

<A NAME="RA38505ST-49">49</A> Montenegro E. Moyano A. Pericas MA. Riera A. Alvarez-Larena A. Piniella J.-F. Tetrahedron: Asymmetry 1999, 10: 457

<A NAME="RA38505ST-50">50</A> Fonquerna S. Rios R. Moyano A. Pericas MA. Riera A. Eur. J. Org. Chem. 1999, 3459

<A NAME="RA38505ST-51">51</A> Shen L. Hsung RP. Tetrahedron Lett. 2003, 44: 9353

<A NAME="RA38505ST-52">52</A> Sola J. Riera A. Pericas MA. Verdaguer X. Maestro MA. Tetrahedron Lett. 2004, 45: 5387

<A NAME="RA38505ST-53">53</A> Balsells J. Vazquez J. Moyano A. Pericas MA. Riera A. J. Org. Chem. 2000, 65: 7291

<A NAME="RA38505ST-54A">54a</A> Fonquerna S. Moyano A. Pericas MA. Riera A. J. Am. Chem. Soc. 1997, 119: 10225

<A NAME="RA38505ST-54B">54b</A> Vazquez J. Fonquerna S. Moyano A. Pericas MA. Riera A. Tetrahedron: Asymmetry 2001, 12: 1837

<A NAME="RA38505ST-55A">55a</A> Verdaguer X. Moyano A. Pericas MA. Riera A. Bernardes V. Greene AE. Alvarez-Larena A. Piniella JF. J. Am. Chem. Soc. 1994, 116: 2153

<A NAME="RA38505ST-55B">55b</A> Fonquerna S. Moyano A. Pericas MA. Riera A. Tetrahedron 1995, 51: 4239

<A NAME="RA38505ST-55C">55c</A> Montenegro E. Poch M. Moyano A. Pericas MA. Riera A. Tetrahedron Lett. 1998, 39: 335

<A NAME="RA38505ST-55D">55d</A> Verdaguer X. Vazquez J. Fuster G. Bernardes-Genisson V. Greene AE. Moyano A. Pericas MA. Riera A. J. Org. Chem. 1998, 63: 7037

<A NAME="RA38505ST-55E">55e</A> Verdaguer X. Moyano A. Pericas MA. Riera A. Alvarez-Larena A. Piniella J.-F. Organometallics 1999, 18: 4275

<A NAME="RA38505ST-55F">55f</A> Marchueta I. Montenegro E. Panov D. Poch M. Verdaguer X. Moyano A. Pericas MA. Riera A. J. Org. Chem. 2001, 66: 6400

<A NAME="RA38505ST-56">56</A> Hiroi utilized methionine-derived amides as auxiliaries. See: Hiroi K. Watanabe T. Tetrahedron Lett. 2000, 41: 3935

<A NAME="RA38505ST-57">57</A> Fletcher AJ. Fryatt R. Rutherford DT. Christie SDR. Tetrahedron Lett. 2004, 45: 5247

<A NAME="RA38505ST-58">58</A> Rios R. Pericas MA. Moyano A. Tetrahedron Lett. 2002, 43: 4903

<A NAME="RA38505ST-59">59</A> Rios R. Pericas MA. Moyano A. Maestro MA. Mahia J. Org. Lett. 2002, 4: 1205

<A NAME="RA38505ST-60A">60a</A> Bladon P. Pauson PL. Brunner H. Eder R. J. Organomet. Chem. 1988, 355: 449

<A NAME="RA38505ST-60B">60b</A> Brunner H. Niedernhuber A. Tetrahedron: Asymmetry 1990, 1: 707

<A NAME="RA38505ST-61A">61a</A> Hay AM. Kerr WJ. Kirk GG. Middlemiss D. Organometallics 1995, 14: 4986

<A NAME="RA38505ST-61B">61b</A> Kerr WJ. Kirk GG. Middlemiss D. J. Organomet. Chem. 1996, 519: 93

<A NAME="RA38505ST-62">62</A> Bonnet J.-J. Mathieu R. Inorg. Chem. 1978, 17: 1973

<A NAME="RA38505ST-63">63</A> Bird PH. Fraser AR. Hall DN. Inorg. Chem. 1977, 16: 1923

<A NAME="RA38505ST-64">64</A> Chia LS. Cullen WR. Franklin M. Manning AR. Inorg. Chem. 1975, 14: 2521

<A NAME="RA38505ST-65">65</A> Derdau V. Laschat S. Dix I. Jones PG. Organometallics 1999, 18: 3859

<A NAME="RA38505ST-66">66</A> Sell T. Laschat S. Dix I. Jones PG. Eur. J. Org. Chem. 2000, 4119

<A NAME="RA38505ST-67">67</A> Monsees A. Laschat S. Synlett 2002, 1011

<A NAME="RA38505ST-68">68</A> Gibson SE. Kaufmann KAC. Loch JA. Steed JW. White AJP. Chem.-Eur. J. 2005, 11: 2566

<A NAME="RA38505ST-69">69</A> Gimbert Y. Robert F. Durif A. Averbuch M.-T. Kann M. Greene AE. J. Org. Chem. 1999, 64: 3492

<A NAME="RA38505ST-70">70</A> Konya D. Robert F. Gimbert Y. Greene AE. Tetrahedron Lett. 2004, 45: 6975

<A NAME="RA38505ST-71">71</A> Castro J. Moyano A. Pericas MA. Riera A. Maestro MA. Mahia J. Organometallics 2000, 19: 1704

<A NAME="RA38505ST-72">72</A> Poulton AM. Christie SDR. Fryatt R. Dale SH. Elsegood MRJ. Andrews DM. Synlett 2004, 2103

<A NAME="RA38505ST-73A">73a</A> Castro J. Moyano A. Pericas MA. Riera A. Alvarez-Larena A. Piniella JF. J. Organomet. Chem. 1999, 585: 53

<A NAME="RA38505ST-73B">73b</A> Castro J. Moyano A. Pericas MA. Riera A. Alvarez-Larena A. Piniella JF. J. Am. Chem. Soc. 2000, 122: 7944

<A NAME="RA38505ST-74A">74a</A> Verdaguer X. Moyano A. Pericas MA. Riera A. Maestro MA. Mahia J. J. Am. Chem. Soc. 2000, 122: 10242

<A NAME="RA38505ST-74B">74b</A> Verdaguer X. Lledo A. Lopez-Mosquera C. Maestro MA. Pericas MA. Riera A. J. Org. Chem. 2004, 69: 8053

<A NAME="RA38505ST-75">75</A> Verdaguer X. Pericas MA. Riera A. Maestro MA. Mahia J. Organometallics 2003, 22: 1868

<A NAME="RA38505ST-76">76</A> Edwards AJ. Mack SR. Mays MJ. Mo C.-Y. Raithby PR. Rennie M.-A. J. Organomet. Chem. 1996, 519: 243

<A NAME="RA38505ST-77">77</A> Kerr WJ. Kirk GG. Middlemiss D. Synlett 1995, 1085

<A NAME="RA38505ST-78">78</A> Derdau V. Laschat S. Jones PG. Heterocycles 1998, 48: 1445

<A NAME="RA38505ST-79">79</A> Derdau V. Laschat S. J. Organomet. Chem. 2002, 642: 131

<A NAME="RA38505ST-80">80</A> Carpenter NE. Nicholas KM. Polyhedron 1999, 18: 2027

<A NAME="RA38505ST-81A">81a</A> Kerr WJ. Lindsay DM. Rankin EM. Scott JS. Watson SP. Tetrahedron Lett. 2000, 41: 3229

<A NAME="RA38505ST-81B">81b</A> Carbery DR. Kerr WJ. Lindsay DM. Scott JS. Watson SP. Tetrahedron Lett. 2000, 41: 3235

<A NAME="RA38505ST-82">82</A> Khand IU. Knox GR. Pauson PL. Watts WE. Foreman MI. J. Chem. Soc., Perkin Trans. 1 1973, 977

<A NAME="RA38505ST-83">83</A> Rautenstrauch V. Megard P. Conesa J. Küster W. Angew. Chem., Int. Ed. Engl. 1990, 29: 1413 ; Angew. Chem. 1990, 102, 1441

<A NAME="RA38505ST-84">84</A> Hicks FA. Kablaoui NM. Buchwald SL. J. Am. Chem. Soc. 1996, 118: 9450

<A NAME="RA38505ST-85">85</A> Hicks FA. Buchwald SL. J. Am. Chem. Soc. 1996, 118: 11688

<A NAME="RA38505ST-86">86</A> Hicks FA. Kablaoui NM. Buchwald SL. J. Am. Chem. Soc. 1999, 121: 5881

<A NAME="RA38505ST-87A">87a</A> Pagenkopf BL. Livinghouse T. J. Am. Chem. Soc. 1996, 118: 2285

<A NAME="RA38505ST-87B">87b</A> Belanger DB. O’Mahony DJR. Livinghouse T. Tetrahedron Lett. 1998, 39: 7637

<A NAME="RA38505ST-88">88</A> Lee NY. Chung YK. Tetrahedron Lett. 1996, 37: 3145

<A NAME="RA38505ST-89A">89a</A> Rajesh T. Periasamy M. Tetrahedron Lett. 1999, 40: 817

<A NAME="RA38505ST-89B">89b</A> Rajesh T. Periasamy M. Organometallics 1999, 18: 5709

<A NAME="RA38505ST-90">90</A> Sugihara T. Yamaguchi M. J. Am. Chem. Soc. 1998, 120: 10782

<A NAME="RA38505ST-91">91</A> Jeong N. Hwang SH. Lee YW. Lim JS. J. Am. Chem. Soc. 1997, 119: 10549

<A NAME="RA38505ST-92">92</A> Jeong N. Hwang SH. Angew. Chem. Int. Ed. 2000, 39: 636 ; Angew. Chem. 2000, 112, 650

<A NAME="RA38505ST-93">93</A> Sugihara T. Yamaguchi M. Synlett 1998, 1384

<A NAME="RA38505ST-94">94</A> Krafft ME. Bonaga LVR. Hirosawa C. J. Org. Chem. 2001, 66: 3004

<A NAME="RA38505ST-95">95</A> Hayashi M. Hashimoto Y. Yamamoto Y. Usuki J. Saigo K. Angew. Chem. Int. Ed. 2000, 39: 631 ; Angew. Chem. 2000, 112, 645

<A NAME="RA38505ST-96">96</A> Fischer S. Groth U. Jung M. Schneider A. Synlett 2002, 2023

<A NAME="RA38505ST-97">97</A> For stoichiometric microwave promoted Pauson-Khand reaction see: Iqbal M. Vyse N. Dauvergne J. Evans P. Tetrahedron Lett. 2002, 43: 7859

<A NAME="RA38505ST-98">98</A> Gibson SE. Mainolfi N. Kalindjian SB. Wright PT. Angew. Chem. Int. Ed. 2004, 43: 5680 ; Angew. Chem. 2004, 116, 5798

<A NAME="RA38505ST-99">99</A> Gibson SE. Johnstone C. Stevenazzi A. Tetrahedron 2002, 58: 4937

<A NAME="RA38505ST-100">100</A> Hiroi K. Watanabe T. Kawagishi R. Abe I. Tetrahedron: Asymmetry 2000, 11: 797

<A NAME="RA38505ST-101">101</A> Kim S.-W. Son SU. Lee SI. Hyeon T. Chung YK. J. Am. Chem. Soc. 2000, 122: 1550

<A NAME="RA38505ST-102">102</A> Tobisu M. Chatani N. Asaumi T. Amako K. Ie Y. Fukumoto Y. Murai S. J. Am. Chem. Soc. 2000, 122: 12663

<A NAME="RA38505ST-103">103</A> Chatani N. Tobisu M. Asaumi T. Murai S. Synlett 2000, 925

<A NAME="RA38505ST-104">104</A> Kondo T. Nakamura A. Okada T. Suzuki N. Wada K. Mitsudo T. J. Am. Chem. Soc. 2000, 122: 6319

<A NAME="RA38505ST-105">105</A> Morisaki Y. Kondo T. Mitsudo T. Org. Lett. 2000, 2: 949

<A NAME="RA38505ST-106">106</A> Kobayashi T. Koga Y. Narasaka K. J. Organomet. Chem. 2001, 624: 73

<A NAME="RA38505ST-107">107</A> Park KH. Son SU. Chung YK. Tetrahedron Lett. 2003, 44: 2827

<A NAME="RA38505ST-108">108</A> Wender PA. Deschamps NM. Williams TJ. Angew. Chem. Int. Ed. 2004, 43: 3076 ; Angew. Chem. 2004, 116, 3138

<A NAME="RA38505ST-109">109</A> Park KH. Jung IG. Chung YK. Org. Lett. 2004, 6: 1183

<A NAME="RA38505ST-110">110</A> Park KH. Son SU. Chung YK. Chem. Commun. 2003, 1898

<A NAME="RA38505ST-111">111</A> Shibata T. Takagi K. J. Am. Chem. Soc. 2000, 122: 9852

<A NAME="RA38505ST-112">112</A> Jeong N. Sung BK. Choi YK. J. Am. Chem. Soc. 2000, 122: 6771

<A NAME="RA38505ST-113">113</A> Yamanaka M. Nakamura E. J. Am. Chem. Soc. 2001, 123: 1703

<A NAME="RA38505ST-114">114</A> Bitterwolf TE. Scallorn WB. Weiss CA. J. Organomet. Chem. 2000, 605: 7

<A NAME="RA38505ST-115">115</A> Pfletschinger A. Koch W. Schmalz H.-G. Chem.-Eur. J. 2001, 7: 5325

<A NAME="RA38505ST-116">116</A> Gimbert Y. Lasage D. Milet A. Fournier F. Greene AE. Tabet J.-C. Org. Lett. 2003, 5: 4073

<A NAME="RA38505ST-117">117</A> Kaldis JH. Morawietz P. McGlinchey MJ. Organometallics 2003, 22: 1293

<A NAME="RA38505ST-118">118</A> Ajamian A. Gleason JL. Angew. Chem. Int. Ed. 2004, 43: 3754 ; Angew. Chem. 2004, 116, 3842

<A NAME="RA38505ST-119">119</A> Hätzelt A. Laschat S. Can. J. Chem. 2002, 80: 1327

<A NAME="RA38505ST-120A">120a</A> Sasson Y. Rempel GL. Tetrahedron Lett. 1974, 4133

<A NAME="RA38505ST-120B">120b</A> Sasson Y. Blum J. Tetrahedron Lett. 1971, 2167

<A NAME="RA38505ST-121">121</A> Hallman PS. Evans D. Osborn JA. Wilkinson G. J. Chem. Soc., Chem. Commun. 1967, 305

<A NAME="RA38505ST-122">122</A> Krafft ME. Bonaga LVR. Wright JA. Hirosawa C. J. Org. Chem. 2002, 67: 1233