Lewis acid-promoted carbonyl addition of lithium (α- carbalkoxyvinyl)cuprates to aldehydes provides a novel asymmetric synthesis of β,β-disubstituted α-(hydroxyalkyl)acrylates

Tetrahedron Letters

Volumn 39, Issue 45, 1998, Pages 8203-8206

  Wei, Han Xun ^a   Willis, Steven ^a   Li, Guigen ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032487992     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01875-9     Document Type: Article

References (22)

1. 1. a) Ciganek, E. Org. React. 1997, 57, 201;
2. b) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001;
3. c) Drewes, S. E.; Roos, G. H. Tetrahedron 1988, 44, 4653.
4. 2. a) Brzezinski, L. J.; Rafel, S.; Leahy, J. M. J. Am. Chem. Soc. 1997, 119, 4317;
5. b) Marko, I. E.; Giles, P. G.; Hindley, N. J. Tetrahedron 1997, 53, 1015;
6. c) Aggarwal, V.; Tarver, G. J. McCague, R. J. Chem. Soc. Chem. Commun. 1996, 2713;
7. d) Oishi, T.; Oguri, H.; Hirama, M. Tetrahedron Asymmetry 1995, 6, 1241.
8. 3. a) Marino, J. P.; Linderman, R. J. J. Org. Chem. 1983, 48, 4621;
9. b) Li, G.; Wei, H.-X.; Willis, S. to be published.
10. 4. a) Tsuda, T.; Yoshida, T.; T. Kawamoto; Saegusa, T. J. Org. Chem. 1987, 52, 1624;
11. b) Li, G.; Wei, H.-X.; Willis, S. Tetrahedron Lett. 1998, 39, 4607.
12. 5. Genisson, Y.; Massardier, C.; Gautier-Luneau, I.; A. E. Greene J. Chem. Soc., Perkin Trans I 1996, 2869.
13. 6. Li, G.; Wei, H.-X.; Whittlesey, B. R.; Batrice, N. N. to be published.
14. 7. Corey, E. J.; Katzenellebogen, J. A. J. Am. Chem. Soc. 1969, 91, 1851.
15. 8. Siddall, J. B.; Biskup, M.; Fried, J. H. J. Am. Chem. Soc. 1969, 91, 1853. For recent reviews about organocopper reagents see 9-12:
16. 9. Lipshutz, B. H. in Comprehensive Organic Synthesis (Eds. Trost, B. M.; Fleming, I.), vol. 1, Pergamon, Oxford, 1991, pp. 107-138.
17. 10. Gilbert, A.; Heritage, T. W.; Isaacs, N. S. Tetrahedron: Asymmetry 1991, 2, 969.
18. 11. Lipshutz, B. H.; Sengupta, S. in Org. React. 1992, 41, 135.
19. 12. Krause, N.; Gerold, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 187.
20. 13. a) Carlsen, P. H. J.; Katsuki, T.; Martin, S. V.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936;
21. b) Martin, S. V.; Nunez, M. T. J. Org. Chem. 1990, 55, 1928.
22. -1, 11.47 min (S), 15.66 min (R).