Novel (trimethylgermyl)copper(I) reagents: Preparation and addition to α,β-unsaturated ketones and α,β-alky nie Esters

Organometallics

Volumn 17, Issue 19, 1998, Pages 4213-4217

  Piers, Edward ^a   Lemieux, René M ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042248631     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980537+     Document Type: Article

References (23)

1. (a) Piers, E.; Marais, P. C. J. Chem. Soc., Chem. Commun. 1989, 1222.
2. (b) Piers, E.; Marais, P. C. J. Org. Chem. 1990, 55, 3454.
3. (c) Piers, E.; Renaud, J. J. Org. Chem. 1993, 58, 11.
4. (d) Piers, E.; Oballa, R. M. Tetrahedron Lett. 1995, 36, 5857.
5. (e) Piers, E.; Kaller, A. M. Synlett 1996, 549.
6. Piers, E.; Lemieux, R. Organometallics 1995, 14, 5011.
7. Oda, H.; Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1984, 25, 3217.
8. Bravo-Zhivotovskii, D. A.; Pigarev, S. D.; Kalikhman, I. D.; Vyazankina, O. A.; Vyazankin, N. S. J. Organomet. Chem. 1983, 248, 51.
9. Yamaguchi, J.-i.; Tamada, Y.; Takeda, T. Bull. Chem. Soc. Jpn. 1993, 66, 607.
10. The formulas 25 are not meant to portray actual structures but are based on the relative amounts of reactants employed in the preparation of the reagents and on the "traditional" protocol employed to represent cuprates. See: (a) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135. (b) Lipshutz, B. H. Acc. Chem. Res. 1997, 30, 277. (c) Nakamura, E.; Mori, S.; Nakamura, M.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4887 and references therein, (d) Bertz, S. H.; Nilsson, K.; Davidsson, O.; Snyder, J. P. Angew. Chem., Int. Ed. Engl. 1998, 37, 314 and references therein.
11. The formulas 25 are not meant to portray actual structures but are based on the relative amounts of reactants employed in the preparation of the reagents and on the "traditional" protocol employed to represent cuprates. See: (a) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135. (b) Lipshutz, B. H. Acc. Chem. Res. 1997, 30, 277. (c) Nakamura, E.; Mori, S.; Nakamura, M.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4887 and references therein, (d) Bertz, S. H.; Nilsson, K.; Davidsson, O.; Snyder, J. P. Angew. Chem., Int. Ed. Engl. 1998, 37, 314 and references therein.
12. The formulas 25 are not meant to portray actual structures but are based on the relative amounts of reactants employed in the preparation of the reagents and on the "traditional" protocol employed to represent cuprates. See: (a) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135. (b) Lipshutz, B. H. Acc. Chem. Res. 1997, 30, 277. (c) Nakamura, E.; Mori, S.; Nakamura, M.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4887 and references therein, (d) Bertz, S. H.; Nilsson, K.; Davidsson, O.; Snyder, J. P. Angew. Chem., Int. Ed. Engl. 1998, 37, 314 and references therein.
13. The formulas 25 are not meant to portray actual structures but are based on the relative amounts of reactants employed in the preparation of the reagents and on the "traditional" protocol employed to represent cuprates. See: (a) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135. (b) Lipshutz, B. H. Acc. Chem. Res. 1997, 30, 277. (c) Nakamura, E.; Mori, S.; Nakamura, M.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4887 and references therein, (d) Bertz, S. H.; Nilsson, K.; Davidsson, O.; Snyder, J. P. Angew. Chem., Int. Ed. Engl. 1998, 37, 314 and references therein.
14. Still, W. C. J. Am. Chem. Soc. 1977, 99, 4836.
15. Piers, E.; Oballa, R. M. J. Org. Chem. 1996, 61, 8439 and references therein.
16. Alexakis, A.; Normant, J. J. Organomet. Chem. 1975, 96, 471.
17. Normant, J. F.; Bourgain, M. Tetrahedron Lett. 1971, 27, 2583.
18. Normant, J. F.; Alexakis, A. Synthesis 1981, 841.
19. 3SnCu(SPh)Li with alkyl alk-2-ynoates: Piers, E.; Chong, J. M.; Morton, H. E. Tetrahedron 1989, 45, 363.
20. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: New York, 1988.
21. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
22. Taber, D. F. J. Org. Chem. 1982, 47, 1351.
23. Piers, E.; Friesen, R. W.; Rettig, S. J. Can. J. Chem. 1992, 70, 1385.