Preparation and Synthetic Transformation of Alkenyl Carbamates into Vinyl Zirconocene Derivatives

Helena Chechik-Lankin; Ilan Marek

doi:10.1055/s-2005-918436

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Synthesis 2005(19): 3311-3318
DOI: 10.1055/s-2005-918436

PAPER

Preparation and Synthetic Transformation of Alkenyl Carbamates into Vinyl Zirconocene Derivatives

Helena Chechik-Lankin, Ilan Marek*
The Mallat Family Laboratory in Organic Chemistry, Department of Chemistry, Institute of Catalysis Science and Technology, The Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Haifa 32 000, Israel
e-Mail: chilanm@tx.technion.ac.il;

Further Information

Publication History

Received 15 September 2005
Publication Date:
27 October 2005 (online)

Abstract
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Abstract

The carbocupration reaction of alkynyl carbamates leads to the stereospecific preparation of polysubstituted alkenyl carbamates. Subsequent treatment of these enol carbamates with the Negishi reagent gave the corresponding vinyl zirconocene species.

Keywords

alkynyl carbamates - vinyl zirconocene derivatives - organocopper reagents

References

1 Liard A. Marek I. J. Org. Chem. 2000, 65: 7218

Crossref Google Scholar
2 Liard A. Kaftanov J. Chechik H. Farhat S. Morlender-Vais N. Averbuj C. Marek I. J. Organomet. Chem. 2001, 624: 26

Crossref Google Scholar
3 Farhat S. Marek I. Angew. Chem. Int. Ed. 2001, 624: 1410

Google Scholar
4a Farhat S. Zouev I. Marek I. Tetrahedron 2004, 60: 1329

Article in Thieme Connect Google Scholar
4b Chinkov N. Chechik H. Majumdar S. Liard A. Marek I. Synthesis 2002, 2473

Article in Thieme Connect Google Scholar
5a Chinkov N. Majumdar S. Marek I. J. Am. Chem. Soc. 2002, 124: 10282

Crossref Google Scholar
5b Canchegui B. Bertus P. Szymoniak J. Synlett 2001, 123

Crossref Google Scholar
5c Nicka N. Majumdar S. Marek I. J. Am. Chem. Soc. 2003, 125: 13258

Crossref Google Scholar
6 Chinkov N. Marek I. In Stereoselective Synthesis of Dienyl Zirconocene Complexes, In Topics in Organometallic Chemistry 10: Marek I. Springer-Verlag; Berlin/ Heidelberg: 2004. p.133

Google Scholar
For reviews, see
7a Negishi E. Takahashi T. Bull. Chem. Soc. Jpn. 1988, 71: 755

Google Scholar
7b Negishi E. Takahashi T. Acc. Chem. Res. 1994, 27: 124

Google Scholar
7c Negishi E. Kondakov DY. Chem. Soc. Rev. 1996, 26: 417

Google Scholar
8 Titanium and Zirconium in Organic Synthesis Marek I. Wiley-VCH; Weinheim: 2002.

Google Scholar
9 Ward AS. Mintz EA. Kramer MP. Organometallics 1988, 7: 8

Crossref Google Scholar
10a Hense T. Hoppe D. Angew. Chem. Int. Ed. 1997, 36: 2282

Crossref Google Scholar
10b Kerrick ST. Beak P. J. Am. Chem. Soc. 1991, 113: 9708

Crossref Google Scholar
11a Hoppe D. Hanko R. Bronneke A. Lichtenberg F. van Hulsen E. Chem. Ber. 1985, 118: 2822

Google Scholar
11b Berque I. Le Menez P. Razon P. Anies C. Pancrazi A. Ardisson J. Neuman A. Prange T. Brion JD. Synlett 1988, 1135

Google Scholar
12a Pimm A. Kocienski P. Street SDA. Synlett 1992, 886

Article in Thieme Connect Google Scholar
12b Ferezou JP. Julia M. Li Y. Liu LW. Pancrazi A. Bull. Soc. Chim. Fr. 1995, 132: 428

Article in Thieme Connect Google Scholar
12c Smith ND. Kocienski PJ. Street SDA. Synthesis 1996, 652

Article in Thieme Connect Google Scholar
13a Hoppe D. Angew. Chem., Int. Ed. Engl. 1984, 23: 932

Crossref Google Scholar
13b Hoppe D. Zschage O. Angew. Chem., Int. Ed. Engl. 1989, 28: 69

Crossref Google Scholar
13c Zschage O. Hoppe D. Tetrahedron 1992, 48: 8389

Crossref Google Scholar
13d Hoppe D. Hense T. Angew. Chem. Int. Ed. 1997, 36: 2282

Crossref Google Scholar
13e Paulsen H. Hoppe D. Tetrahedron 1992, 48: 5667

Crossref Google Scholar
13f Berque I. Le Menez P. Razon P. Mahuteau J. Ferezou JP. Pancrazi A. Ardisson J. Brion JD. J. Org. Chem. 1999, 64: 373

Crossref Google Scholar
14a Kocienski P. Dixon NJ. Synlett 1989, 52

Crossref Google Scholar
14b Wadman S. Whitby R. Yeates C. Kocienski P. Cooper K. J. Chem. Soc., Chem. Commun. 1987, 241

Crossref Google Scholar
14c Poree FH. Clavel A. Betzer JF. Pancrazi A. Ardisson J. Tetrahedron Lett. 2003, 44: 7553

Crossref Google Scholar
15 Madec D. Pujol S. Henryon V. Ferezou JP. Synlett 1995, 435

Article in Thieme Connect Google Scholar
16 Madec D. Henryon V. Ferezou JP. Tetrahedron Lett. 1999, 40: 8103

Crossref Google Scholar
17 Poree FH. Barbion J. Dhulut S. Betzer JF. Pancrazi A. Ardisson J. Synthesis 2004, 3017

Article in Thieme Connect Google Scholar
For mixture of isomers, see:
18a Olofson RA, Wooden GP, and Marks JT. inventors; Eur. Pat. 104984. ; Chem. Abstr. 1984, 101, 190657u

Crossref Google Scholar
18b Franco-Filipasic BR. Patarcity R. Chem. Ind. 1969, 8: 166

Crossref Google Scholar
18c Shimizu M. Tanaka E. Yoshioka H. J. Chem. Soc., Chem. Commun. 1987, 136

Crossref Google Scholar
18d Olofson RA. Schnur RC. Bunes L. Pepe JP. Tetrahedron Lett. 1977, 1567

Crossref Google Scholar
18e Lee LH. J. Org. Chem. 1965, 30: 3943

Crossref Google Scholar
18f Olofson RA. Bauman BA. Vancowicz DJ. J. Org. Chem. 1978, 43: 752

Crossref Google Scholar
18g Mahe R. Dixneuf PH. Lecolier S. Tetrahedron Lett. 1986, 27: 6333

Crossref Google Scholar
18h Mahe R. Sasaki Y. Bruneau C. Dixneuf PH. J. Org. Chem. 1989, 54: 1518

Crossref Google Scholar
18i Hofer J. Doucet H. Bruneau C. Dixneuf PH. Acc. Chem. Res. 1999, 32: 311

Crossref Google Scholar
18j Rohr M. Geyer C. Wandeler R. Schneider MS. Murphy EF. Baiker A. Green Chem. 2001, 3: 123

Crossref Google Scholar
18k Sengupta S. Snieckus V. J. Org. Chem. 1990, 55: 5680

Crossref Google Scholar
18l Superchi S. Sotomayor N. Miao G. Joseph B. Snieckus V. Tetrahedron Lett. 1996, 37: 6057

Crossref Google Scholar
18m Superchi S. Sotomayor N. Miao G. Joseph B. Campbell MG. Snieckus V. Tetrahedron Lett. 1996, 37: 6061

Crossref Google Scholar
For recent reviews on carbometallation reactions, see:
19a Marek I. Chinkov N. Banon-Tenne D. In Carbometallation Reactions, In Metal-Catalyzed Cross-Coupling Reactions de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004. p.395

Crossref Google Scholar
19b Banon-Tenne D. Marek I. In Carbometallation Reactions of Zinc Enolate Derivatives, In Transition Metals for Organic Synthesis Beller M. Bolm C. Wiley-VCH; Weinheim: 2004. p.563

Crossref Google Scholar
19c Marek I. J. Chem. Soc., Perkin. Trans. 1 1999, 535

Crossref Google Scholar
20 Normant JF. Alexakis A. Synthesis 1981, 841

Article in Thieme Connect Google Scholar
For theoretical calculations, see:
21a Nakamura E. Mori S. Morokuma K. J. Am. Chem. Soc. 1997, 119: 4887

Google Scholar
21b Mori S. Nakamura E. J. Mol. Struct. 1999, 5: 1534

Google Scholar
22 Achyutha Rao S. Knochel P. J. Am. Chem. Soc. 1992, 114: 7579

Crossref Google Scholar
23a Normant JF. Alexakis A. Commercon A. Cahiez G. Villieras J. C. R. Seances Acad. Sci., Ser. C 1974, 279: 763

Google Scholar
23b Vermeer P. Meijer J. de Graaf C. Recl. Trav. Chim. Pays-Bas 1974, 93: 24

Google Scholar
23c Meijer J. Westmijze H. Vermeer P. Recl. Trav. Chim. Pays-Bas 1976, 95: 102

Google Scholar
23d Alexakis A. Cahiez G. Normant J. Villieras J. Bull. Soc. Chim. Fr. 1977, 693

Google Scholar
24a Gralla G. Wibbeling B. Hoppe D. Org. Lett. 2002, 4: 2193

Crossref Google Scholar
24b Gralla G. Wibbeling B. Hoppe D. Tetrahedron Lett. 2003, 44: 8979

Crossref Google Scholar
24c Hoppe D. Gonschorrek C. Tetrahedron Lett. 1987, 28: 785

Crossref Google Scholar
24d Egert E. Beck H. Schmidt D. Gonschorrek C. Hoppe D. Tetrahedron Lett. 1987, 28: 789

Crossref Google Scholar
25 Chechik-Lankin H. Marek I. Org. Lett. 2003, 5: 5087

Crossref PubMed Google Scholar
For some similar examples, see:
26a Alexakis A. Normant JF. Villieras J. J. Organomet. Chem. 1975, 96: 471

Crossref Google Scholar
26b Alexakis A. Normant JF. Villieras J. J. Mol. Catal. 1975, 1: 43

Crossref Google Scholar
26c Alexakis A. Commercon A. Coulentianos C. Normant JF. Tetrahedron 1984, 40: 715

Crossref Google Scholar
27 Hoveyda A. Evans DA. Fu GC. Chem. Rev. 1993, 93: 1307

Crossref Google Scholar
28a Marek I. Chem. Rev. 2000, 100: 2887

Crossref Google Scholar
28b Averbuj C. Kaftanov J. Marek I. Synlett 1999, 1939

Crossref Google Scholar
28c Kaftanov J. Averbuj C. Vais-Morlender N. Liard A. Marek I. Polyhedron 2000, 19: 563

Crossref Google Scholar
29 On HP. Lewis W. Zweifel G. Synthesis 1981, 999 ; 1-hexene-1E-iodo, registry number: 16644-98-7

Article in Thieme Connect Google Scholar
30a Brown HC. Somayaji V. Richard B. Synthesis 1984, 919

Google Scholar
30b Alexakis A. Cahiez G. Normant JF. Org. Synth. 1990, Vol. VII: 290 , 1-hexene-1E-iodo, registry number: 16644-98-7

Google Scholar