A novel method for asymmetric synthesis of both enantiomers of α-substituted carboxylic acid derivatives from optically active 1-chlorovinyl p-tolyl sulfoxides and lithium ester enolates with 1,4-chiral induction from the sulfur chiral center

Tetrahedron Letters

Volumn 46, Issue 39, 2005, Pages 6771-6775

  Sugiyama, Shimpei ^a   Kido, Masahiro ^a   Satoh, Tsuyoshi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

1,4 Chiral induction; Asymmetric synthesis; Lithium ester enolate; Optically active substituted ester; Optically active sulfoxide

Indexed keywords

CARBOXYLIC ACID; ESTER DERIVATIVE; KETONE; LITHIUM; SULFOXIDE; SULFUR; VINYL DERIVATIVE;

ADDITION REACTION; ARTICLE; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; METHODOLOGY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 23944504255     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.172     Document Type: Article

References (37)

1. Some monographs for the chemistry of carboxylic acids, amides, lactones, and their derivatives: S. Patai The Chemistry of Carboxylic Acids and Esters 1969 John Wiley and Sons London
2. J. Zabicky The Chemistry of Amides 1970 John Wiley and Sons London
3. S. Patai The Chemistry of Acid Derivatives 1979 John Wiley and Sons Chichester Part 1 and 2
4. I.O. Sutherland Comprehensive Organic Chemistry Vol. 2 1979 Pergamon Press Oxford Part 9
5. S. Patai The Chemistry of Acid Derivatives 1992 John Wiley and Sons Chichester Part 1 and 2
6. Recent monographs and reviews for the chemistry and synthesis of α-amino acids: G.C. Barrett Chemistry and Biochemistry of the Amino Acids 1985 Chapman and Hall London
7. R.M. Williams Synthesis of Optically Active α-Amino Acids 1989 Pergamon Press Oxford
8. C. Cativiela, and M.D. Diaz-de-Villegas Tetrahedron: Asymmetry 11 2000 645
9. M. Beller, and M. Eckert Angew. Chem., Int. Ed. 39 2000 1010
10. C.H. Heathcock The Aldol Addition Reaction J.D. Morrison Asymmetric Synthesis Vol. 3 1984 Academic Press Orland 111 212 Part B
11. M. Nerz-Stormes, and E.R. Thornton J. Org. Chem. 56 1991 2489
12. M.A. Walker, and C.H. Heathcock J. Org. Chem. 56 1991 5747
13. D.A. Evans, M.T. Bilodeau, T.C. Somers, J. Clardy, D. Cherry, and Y. Kato J. Org. Chem. 56 1991 5750
14. Some recent papers concerning this chemistry: T. Shioiri Farumashia 33 1997 599
15. M. Horikawa, J. Busch-Petersen, and E.J. Corey Tetrahedron Lett. 40 1999 3843
16. A. Nelson Angew. Chem., Int. Ed. 38 1999 1583
17. T. Ooi, M. Kameda, H. Tannai, and K. Maruoka Tetrahedron Lett. 41 2000 8339
18. K. Juhl, and K.A. Jorgensen J. Am. Chem. Soc. 124 2002 2420
19. S.-S. Jew, B.-S. Jeong, J.-H. Lee, M.-S. Yoo, Y.-J. Lee, B.-S. Park, M.G. Kim, and H.-G. Park J. Org. Chem. 68 2003 4514
20. B.M. Trost, and C. Jiang Org. Lett. 5 2003 1563
21. T. Ooi, and K. Maruoka J. Synth. Org. Chem. Jpn. 61 2003 1195
22. T. Ooi, Y. Uematsu, and K. Maruoka Tetrahedron Lett. 45 2004 1675
23. E.J. Park, M.H. Kim, and D.Y. Kim J. Org. Chem. 69 2004 6897
24. T. Satoh, S. Sugiyama, and H. Ota Tetrahedron Lett 43 2002 3033
25. T. Satoh, S. Sugiyama, Y. Kamide, and H. Ota Tetrahedron 59 2003 4327
26. T. Satoh, Y. Kamide, and S. Sugiyama Tetrahedron 50 2004 11805
27. S. Sugiyama, and T. Satoh Tetrahedron: Asymmetry 16 2005 665
28. T. Satoh, T. Oohara, Y. Ueda, and K. Yamakawa J. Org. Chem. 54 1989 3130
29. T. Satoh, and H. Ota Tetrahedron 56 2000 5113
30. T. Satoh, T. Kawashima, S. Takahashi, and K. Sakai Tetrahedron 59 2003 9599
31. M. Ramaiah Tetrahedron 43 1987 3541
32. T. Satoh, T. Sato, T. Oohara, and K. Yamakawa J. Org. Chem. 54 1989 3973
33. (S)-2,3,3-Trimethylbutyric acid has plus sign for its specific rotation ([ α ] D 23 +39.7 (c 1.0, ethanol)): M.V. Rangaishenvi, B. Singaram, and H.C. Brown J. Org. Chem. 56 1991 3286
34. D. Seebach, R. Amstutz, T. Laube, W.B. Schweizer, and J.D. Dunitz J. Am. Chem. Soc. 107 1985 5403
35. R.E. Ireland, P. Wipf, and J.D. Armstrong III J. Org. Chem. 56 1991 650
36. F. Tanaka, and K. Fuji Tetrahedron Lett. 33 1992 7885
37. J. Otera, Y. Fujita, and S. Fukuzumi Synlett 1994 213