Asymmetric Wittig Type Reactions

Tobias Rein; Torben M. Pedersen

doi:10.1055/s-2002-23535

REVIEW

Asymmetric Wittig Type Reactions

Tobias Rein*^a,b,c, Torben M. Pedersen^c,d
^a AstraZeneca R&D Södertälje, Discovery Chemistry, 15185 Södertälje, Sweden¹
Fax: +46(8)55328892; e-Mail: Tobias.Rein@astrazeneca.com;
^b Department of Chemistry, Organic Chemistry, Royal Institute of Technology, 10044 Stockholm, Sweden
^c Department of Chemistry, Technical University of Denmark, Building 201, Kemitorvet, 2800 Kgs. Lyngby, Denmark
^d Department of Chemistry, Stanford University, Stanford, California 94305, USA¹

Abstract

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Abstract

The Wittig reaction and related methods for synthesis of C=C double bonds belong to the standard repertoire of the synthetic chemist. Studies of asymmetric versions of these reactions have been increasing in recent years and applications of such processes to complex molecule synthesis have begun to emerge. In this review, we will emphasise the recent advances in developing methods and synthetic applications of these reactions, but earlier results will be covered as well to place the recent results in context.

1 Introduction
2 Reactions with Achiral Monocarbonyl Substrates
2.1 Reactions with Symmetrically Substituted Monoketones
2.2 Synthesis of Chiral Allenes from Ketenes or Acid Halides
3 Reactions with Chiral, Nonracemic Monoketones
4 Kinetic Resolution
4.1 Resolution of Racemic Monocarbonyl Compounds
4.2 Resolution of Racemic Wittig Reagents
5 Dynamic Resolution
6 Other Strategies Based on Resolution of Enantiomers
6.1 Parallel Kinetic Resolution
6.2 Enantioconvergent Synthesis by Sequential Asymmetric HWE Reaction and Palladium-Catalyzed Nucleophilic Allylic Substitution
7 Desymmetrization of Prochiral Dicarbonyl Substrates
8 Future Perspectives, Concluding Remarks

Key words

asymmetric synthesis - asymmetric Wittig reactions - kinetic resolution - enantioconvergent synthesis - desymmetrization

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References

Present address.

<A NAME="RE06201SS-2A">2a</A> Rein T. Reiser O. Acta Chem. Scand. 1996, 50: 369

<A NAME="RE06201SS-2B">2b</A> Li A.-H. Dai W.-M. Aggarwal VK. Chem. Rev. 1997, 97: 2341

<A NAME="RE06201SS-2C">2c</A> Bennani YL. Hanessian S. Chem. Rev. 1997, 97: 3161

<A NAME="RE06201SS-2D">2d</A> Nicolaou KC. Härter MW. Gunzner JL. Nadin A. Liebigs Ann. Recl. 1997, 1283

<A NAME="RE06201SS-2E">2e</A> Wiemer DF. Tetrahedron 1997, 53: 16609

<A NAME="RE06201SS-2F">2f</A> Tanaka K. Fuji K. J. Synth. Org. Chem. Jpn. 1998, 56: 521

<A NAME="RE06201SS-2G">2g</A> Kolodiazhnyi OI. Tetrahedron: Asymmetry 1998, 9: 1279

<A NAME="RE06201SS-2H">2h</A> Tomioka K. Hasegawa M. J. Synth. Org. Chem. Jpn. 2000, 58: 848

<A NAME="RE06201SS-3">3</A> Maryanoff BE. Reitz AB. Chem. Rev. 1989, 89: 863

<A NAME="RE06201SS-4">4</A> Amadji M. Vadecard J. Cahard D. Duhamel L. Duhamel P. Plaquevent J.-C. J. Org. Chem. 1998, 63: 5541 ; see also ref.³³

<A NAME="RE06201SS-5A">5a</A> Johnson CR. Meanwell NA. J. Am. Chem. Soc. 1981, 103: 7667

<A NAME="RE06201SS-5B">5b</A> Erdelmeier I. Gais H.-J. Lindner HJ. Angew. Chem., Int. Ed. Engl. 1986, 25: 935

<A NAME="RE06201SS-6">6</A> Solladié G. Zimmerman R. Bartsch R. Synthesis 1985, 662

<A NAME="RE06201SS-7A">7a</A> Komatsu N. Matsunaga S. Sugita T. Uemura S. J. Am. Chem. Soc. 1993, 115: 5847

<A NAME="RE06201SS-7B">7b</A> Komatsu N. Murakami T. Nishibayashi Y. Sugita T. Uemura S. J. Org. Chem. 1993, 58: 3697

<A NAME="RE06201SS-7C">7c</A> Nishibayashi Y. Singh JD. Uemura S. Tetrahedron Lett. 1994, 35: 3115

<A NAME="RE06201SS-7D">7d</A> Nishibayashi Y. Singh JD. Fukuzawa S.-I. Uemura S. J. Org. Chem. 1995, 60: 4114

<A NAME="RE06201SS-8A">8a</A> Fiaud JC. Legros JY. Tetrahedron Lett. 1988, 29: 2959

<A NAME="RE06201SS-8B">8b</A> Fiaud JC. Legros JY. J. Organomet. Chem. 1989, 370: 383

<A NAME="RE06201SS-8C">8c</A> Legros JY. Fiaud JC. Tetrahedron 1994, 50: 465

<A NAME="RE06201SS-9A">9a</A> Harmat NJS. Warren S. Tetrahedron Lett. 1990, 31: 2743

<A NAME="RE06201SS-9B">9b</A> Clayden J. Warren S. Angew. Chem., Int. Ed. Engl. 1996, 35: 241

<A NAME="RE06201SS-10">10</A> Tömösközi I. Janszó G. Chem. Ind. (London) 1962, 2085

Later results have cast some doubt on the levels of asymmetric induction reported in this paper; see ref. [14a]

<A NAME="RE06201SS-12A">12a</A> Bestmann HJ. Lienert J. Angew. Chem., Int. Ed. Engl. 1969, 8: 763

<A NAME="RE06201SS-12B">12b</A> Bestmann HJ. Heid E. Ryschka W. Lienert J. Liebigs Ann. Chem. 1974, 1684

<A NAME="RE06201SS-13">13</A> Bestmann HJ. Lienert J. Chem.-Ztg. 1970, 94: 487

<A NAME="RE06201SS-14A">14a</A> Hanessian S. Delorme D. Beaudoin S. Leblanc Y. J. Am. Chem. Soc. 1984, 106: 5754

<A NAME="RE06201SS-14B">14b</A> Hanessian S. Beaudoin S. Tetrahedron Lett. 1992, 33: 7655

<A NAME="RE06201SS-14C">14c</A> Hanessian S. Beaudoin S. Tetrahedron Lett. 1992, 33: 7659

<A NAME="RE06201SS-15A">15a</A> Lemieux RP. Schuster GB. J. Org. Chem. 1993, 58: 100

<A NAME="RE06201SS-15B">15b</A> Zhang Y. Schuster GB. J. Org. Chem. 1994, 59: 1855

<A NAME="RE06201SS-15C">15c</A> Suarez M. Schuster GB. J. Am. Chem. Soc. 1995, 117: 6732

<A NAME="RE06201SS-16A">16a</A> Gais H.-J. Schmiedl G. Ball WA. Bund J. Hellmann G. Erdelmeier I. Tetrahedron Lett. 1988, 29: 1773

<A NAME="RE06201SS-16B">16b</A> Gais H.-J. Schmiedl G. Ossenkamp RKL. Liebigs Ann. Recl. 1997, 2419

<A NAME="RE06201SS-17">17</A> Rehwinkel H. Skupsch J. Vorbrüggen H. Tetrahedron Lett. 1988, 29: 1775

<A NAME="RE06201SS-18">18</A> Takahashi T. Matsui M. Maeno N. Koizumi T. Shiro M. Heterocycles 1990, 30: 353

<A NAME="RE06201SS-19">19</A> Toda F. Akai H. J. Org. Chem. 1990, 55: 3446

<A NAME="RE06201SS-20A">20a</A> Denmark SE. Chen C.-T. J. Am. Chem. Soc. 1992, 114: 10674

<A NAME="RE06201SS-20B">20b</A> Denmark S. Rivera I. J. Org. Chem. 1994, 59: 6887

<A NAME="RE06201SS-21">21</A> Furuta T. Iwamura M. J. Chem. Soc., Chem. Commun. 1994, 2167

<A NAME="RE06201SS-22">22</A> Abiko A. Masamune S. Tetrahedron Lett. 1996, 37: 1077

<A NAME="RE06201SS-23">23</A> Kumamoto T. Koga K. Chem. Pharm. Bull. 1997, 45: 753

<A NAME="RE06201SS-24">24</A> Mizuno M. Fujii K. Tomioka K. Angew. Chem. Int. Ed. 1998, 37: 515

<A NAME="RE06201SS-25">25</A> Sano S. Yakugaku Zasshi 2000, 120: 432

<A NAME="RE06201SS-26">26</A> Arai S. Hamaguchi S. Shioiri T. Tetrahedron Lett. 1998, 39: 2997

<A NAME="RE06201SS-27">27</A> Dai W.-M. Wu J. Huang X. Tetrahedron: Asymmetry 1997, 8: 1979

The structure of the alkyl group in the phosphoryl unit was not specified in the original article.

<A NAME="RE06201SS-29">29</A> Bestmann HJ. Tömösközi I. Tetrahedron Lett. 1964, 1293

<A NAME="RE06201SS-30A">30a</A> Musierowicz S. Wroblewski AE. Krawczyk H. Tetrahedron Lett. 1975, 437

<A NAME="RE06201SS-30B">30b</A> Musierowicz S. Wroblewski AE. Tetrahedron 1980, 36: 1375

<A NAME="RE06201SS-31">31</A> Tanaka K. Otsubo K. Fuji K. Tetrahedron Lett. 1996, 37: 3735

<A NAME="RE06201SS-32">32</A> Masamune S. Choy W. Petersen JS. Sita LR. Angew. Chem., Int. Ed. Engl. 1985, 24: 1

<A NAME="RE06201SS-33">33</A> Vaulont I. Gais H.-J. Reuter N. Schmitz E. Ossenkamp RKL. Eur. J. Org. Chem. 1998, 805

<A NAME="RE06201SS-34A">34a</A> Evans DA. Carter PH. Carreira EM. Prunet JA. Charette AB. Lautens M. Angew. Chem. Int. Ed. 1998, 37: 2354

<A NAME="RE06201SS-34B">34b</A> Evans DA. Carter PH. Carreira EM. Charette AB. Prunet JA. Lautens M. J. Am. Chem. Soc. 1999, 121: 7540

<A NAME="RE06201SS-35">35</A> Ohmori K. Ogawa Y. Obitsu T. Ishikawa Y. Nishiyama S. Yamamura S. Angew. Chem. Int. Ed. 2000, 39: 2290

<A NAME="RE06201SS-36">36</A> Tanaka K. Ohta Y. Fuji K. Taga T. Tetrahedron Lett. 1993, 34: 4071 ; this reagent was first introduced within the context of desymmetrization of a meso-diketone (Section 7)

<A NAME="RE06201SS-37A">37a</A> Kagan HB. Fiaud JC. Top. Stereochem. 1988, 18: 249

<A NAME="RE06201SS-37B">37b</A> See also: Kagan HB. Tetrahedron 2001, 57: 2449

<A NAME="RE06201SS-38">38</A> Johnson CR. Elliott RC. Meanwell NA. Tetrahedron Lett. 1982, 23: 5005

The stoichiometry of the reaction, i.e. the ratio of 63:64, was not reported.

The yields given are based on the Wittig type reagent as limiting reactant; 2 equivalents of the substrate were used.

<A NAME="RE06201SS-41">41</A> Rein T. Kann N. Kreuder R. Gangloff B. Reiser O. Angew. Chem. Int. Ed. Engl. 1994, 33: 556

The descriptors R and S refer to the stereocenter originating from the substrate.

<A NAME="RE06201SS-43">43</A> Rein T. Anvelt J. Soone A. Kreuder R. Wulff C. Reiser O. Tetrahedron Lett. 1995, 36: 2303

<A NAME="RE06201SS-44">44</A> Mendlik MT. Cottard M. Rein T. Helquist P. Tetrahedron Lett. 1997, 38: 6375

<A NAME="RE06201SS-45">45</A> Kreuder R. Rein T. Reiser O. Tetrahedron Lett. 1997, 38: 9035

Note that the chiral reagents 14b and 25 all contain the same enantiomer of the chiral auxiliary.

<A NAME="RE06201SS-47">47</A> For a review of different models used for rationalizing the stereoselectivity of such reactions, see: Mengel A. Reiser O. Chem. Rev. 1999, 99: 1191

<A NAME="RE06201SS-48A">48a</A> Norrby P.-O. Brandt P. Rein T. J. Org. Chem. 1999, 64: 5845

<A NAME="RE06201SS-48B">48b</A> For recent computational studies of the parent HWE reaction, see: Brandt P. Norrby P.-O. Martin I. Rein T. J. Org. Chem. 1998, 63: 1280

<A NAME="RE06201SS-48C">48c</A> See also: Ando K. J. Org. Chem. 1999, 64: 6815

For exceptions, see:

Ref. [21] Table 2, entry 1.

Ref. [45] Table 2, entry 12.

<A NAME="RE06201SS-50">50</A> Tanaka K. Watanabe T. Shimamoto K.-Y. Sahakitpichan P. Fuji K. Tetrahedron Lett. 1999, 40: 6599

<A NAME="RE06201SS-51">51</A> Dai W.-M. Lau CW. Tetrahedron Lett. 2001, 42: 2541

<A NAME="RE06201SS-52">52</A> Bestmann HJ. Tömösközi I. Tetrahedron 1968, 24: 3299

The absolute configuration of the product was only tentatively assigned.

<A NAME="RE06201SS-54">54</A> Pinsard P. Lellouche J.-P. Beaucourt J.-P. Grée R. Tetrahedron Lett. 1990, 31: 1137

<A NAME="RE06201SS-55A">55a</A> Noyori R. Tokunaga M. Kitamura M. Bull. Chem. Soc. Jpn. 1995, 68: 36

<A NAME="RE06201SS-55B">55b</A> Ward RS. Tetrahedron: Asymmetry 1995, 6: 1475

<A NAME="RE06201SS-55C">55c</A> Caddick S. Jenkins K. Chem. Soc. Rev. 1996, 25: 447

<A NAME="RE06201SS-56">56</A> Narasaka K. Hidai E. Hayashi Y. Gras J.-L. J. Chem. Soc., Chem. Commun. 1993, 102

<A NAME="RE06201SS-57">57</A> Rein T. Kreuder R. von Zezschwitz P. Wulff C. Reiser O. Angew. Chem., Int. Ed. Engl. 1995, 34: 1023

This can be explained by the fact that the slower reacting enantiomer is continuously racemized and thus not accumulated as in an ordinary kinetic resolution.

<A NAME="RE06201SS-59">59</A> Gante J. Angew. Chem., Int. Ed. Engl. 1994, 33: 1699 ; and references therein

<A NAME="RE06201SS-60A">60a</A> Vedejs E. Chen X. J. Am. Chem. Soc. 1997, 119: 2584

<A NAME="RE06201SS-60B">60b</A> Bertozzi F. Crotti P. Macchia F. Pineschi M. Feringa BL. Angew. Chem. Int. Ed. 2001, 40: 930 ; and references therein

<A NAME="RE06201SS-61">61</A> Pedersen TM. Jensen JF. Humble RE. Rein T. Tanner D. Bodmann K. Reiser O. Org. Lett. 2000, 2: 535

<A NAME="RE06201SS-62">62</A> Pedersen TM. Hansen EL. Rein T. Kane J. Helquist P. Norrby P.-O. Tanner D. J. Am. Chem. Soc. 2001, 123: 9738

This is of course primarily an issue in intermolecular reactions, where the functional groups involved in the reaction can be present in different amounts.

<A NAME="RE06201SS-64">64</A> Schreiber SS. Schreiber TS. Smith DB. J. Am. Chem. Soc. 1987, 109: 1525

<A NAME="RE06201SS-65A">65a</A> Trost BM. Curran DP. J. Am. Chem. Soc. 1980, 102: 5699

<A NAME="RE06201SS-65B">65b</A> Trost BM. Curran DP. Tetrahedron Lett. 1981, 22: 4929

<A NAME="RE06201SS-66">66</A> Later research indicates that the addition step is irreversible also for stabilized ylides, see: Vedejs E. Peterson MJ. Top. Stereochem. 1994, 21: 1

<A NAME="RE06201SS-67">67</A> Tanaka K. Watanabe T. Ohta Y. Fuji K. Tetrahedron Lett. 1997, 38: 8943

<A NAME="RE06201SS-68A">68a</A> Kann N. Rein T. J. Org. Chem. 1993, 58: 3802

<A NAME="RE06201SS-68B">68b</A> Tullis JS. Vares L. Kann N. Norrby P.-O. Rein T. J. Org. Chem. 1998, 63: 8284

<A NAME="RE06201SS-68C">68c</A> Rein T. Vares L. Kawasaki I. Pedersen TM. Norrby P.-O. Brandt P. Tanner D. Phosphorus, Sulfur, and Silicon 1999, 144-146: 169

<A NAME="RE06201SS-69A">69a</A> Vares L. Rein T. Org. Lett. 2000, 2: 2611

Vares, L.; Rein, T., manuscript in preparation.

<A NAME="RE06201SS-70">70</A> Mandai T. Kaihara Y. Tsuji J. J. Org. Chem. 1994, 59: 5847