Stereoselective synthesis of tetra-substituted olefins via addition of zinc enolates to unactivated alkynes

Organic Letters

Volumn 6, Issue 26, 2004, Pages 4837-4840

  Nakamura, Masaharu ^a,b   Fujimoto, Taisuke ^a   Endo, Kohei ^a   Nakamura, Eiichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALKYNE DERIVATIVE; CARBONYL DERIVATIVE; CROTONIC ACID DERIVATIVE; ZINC DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; HYDROLYSIS; ISOMERIZATION; KNOEVENAGEL CONDENSATION; STEREOCHEMISTRY; STOICHIOMETRY; SUBSTITUTION REACTION;

ALKENES; ALKYNES; CATALYSIS; HYDROLYSIS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; ZINC;

EID: 12344269909     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048131i     Document Type: Article

References (21)

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8. Selected papers: (a) Wang, X.; Widenhoefer, R. A. Chem. Commun. 2004, 660-661. (b) Yao, X.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 6884-6885. (c) Karoyan, P.; Quancard, J.; Vaissermann, J.; Chassaing, G. J. Org. Chem. 2003, 68, 2256-2265. (d) Miura, K.; Saito, H.; Fujisawa, N.; Wang, D.; Nishikori, H.; Hosomi, A. Org. Lett. 2001, 3, 4055-4057. (e) Kitagawa, O.; Fujiwara, H.; Suzuki, T.; Taguchi, T.; Shiro, M. J. Org. Chem. 2000, 65, 6819-6825. (f) Lorthiois, E.; Marek, I.; Normant, J. F. J. Org. Chem. 1998, 63, 2442-2450. (g) Yamaguchi, M. Hayashi, A.; Hirama, M. J. Am. Chem. Soc. 1993, 115, 3362-3363.
9. Selected papers: (a) Wang, X.; Widenhoefer, R. A. Chem. Commun. 2004, 660-661. (b) Yao, X.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 6884-6885. (c) Karoyan, P.; Quancard, J.; Vaissermann, J.; Chassaing, G. J. Org. Chem. 2003, 68, 2256-2265. (d) Miura, K.; Saito, H.; Fujisawa, N.; Wang, D.; Nishikori, H.; Hosomi, A. Org. Lett. 2001, 3, 4055-4057. (e) Kitagawa, O.; Fujiwara, H.; Suzuki, T.; Taguchi, T.; Shiro, M. J. Org. Chem. 2000, 65, 6819-6825. (f) Lorthiois, E.; Marek, I.; Normant, J. F. J. Org. Chem. 1998, 63, 2442-2450. (g) Yamaguchi, M. Hayashi, A.; Hirama, M. J. Am. Chem. Soc. 1993, 115, 3362-3363.
10. Selected papers: (a) Wang, X.; Widenhoefer, R. A. Chem. Commun. 2004, 660-661. (b) Yao, X.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 6884-6885. (c) Karoyan, P.; Quancard, J.; Vaissermann, J.; Chassaing, G. J. Org. Chem. 2003, 68, 2256-2265. (d) Miura, K.; Saito, H.; Fujisawa, N.; Wang, D.; Nishikori, H.; Hosomi, A. Org. Lett. 2001, 3, 4055-4057. (e) Kitagawa, O.; Fujiwara, H.; Suzuki, T.; Taguchi, T.; Shiro, M. J. Org. Chem. 2000, 65, 6819-6825. (f) Lorthiois, E.; Marek, I.; Normant, J. F. J. Org. Chem. 1998, 63, 2442-2450. (g) Yamaguchi, M. Hayashi, A.; Hirama, M. J. Am. Chem. Soc. 1993, 115, 3362-3363.
11. Selected papers: (a) Wang, X.; Widenhoefer, R. A. Chem. Commun. 2004, 660-661. (b) Yao, X.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 6884-6885. (c) Karoyan, P.; Quancard, J.; Vaissermann, J.; Chassaing, G. J. Org. Chem. 2003, 68, 2256-2265. (d) Miura, K.; Saito, H.; Fujisawa, N.; Wang, D.; Nishikori, H.; Hosomi, A. Org. Lett. 2001, 3, 4055-4057. (e) Kitagawa, O.; Fujiwara, H.; Suzuki, T.; Taguchi, T.; Shiro, M. J. Org. Chem. 2000, 65, 6819-6825. (f) Lorthiois, E.; Marek, I.; Normant, J. F. J. Org. Chem. 1998, 63, 2442-2450. (g) Yamaguchi, M. Hayashi, A.; Hirama, M. J. Am. Chem. Soc. 1993, 115, 3362-3363.
12. Selected papers: (a) Wang, X.; Widenhoefer, R. A. Chem. Commun. 2004, 660-661. (b) Yao, X.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 6884-6885. (c) Karoyan, P.; Quancard, J.; Vaissermann, J.; Chassaing, G. J. Org. Chem. 2003, 68, 2256-2265. (d) Miura, K.; Saito, H.; Fujisawa, N.; Wang, D.; Nishikori, H.; Hosomi, A. Org. Lett. 2001, 3, 4055-4057. (e) Kitagawa, O.; Fujiwara, H.; Suzuki, T.; Taguchi, T.; Shiro, M. J. Org. Chem. 2000, 65, 6819-6825. (f) Lorthiois, E.; Marek, I.; Normant, J. F. J. Org. Chem. 1998, 63, 2442-2450. (g) Yamaguchi, M. Hayashi, A.; Hirama, M. J. Am. Chem. Soc. 1993, 115, 3362-3363.
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19. 2O/THF). Slightly excess amount of HCl is mandatory to prevent product isomerization.
20. 3 can promote the alkylidenation reaction (69% and 30% yield, respectively) to give a 1: 1 mixture of the geometrical isomers. See also ref 4b,c.
21. Badioli, M.; Ballini, R.; Bartolacci, M.; Bosica, G.; Torregiani, E.; Marcantoni, E. J. Org. Chem. 2002, 67, 8938-8942.