Asymmetric induction in the conjugate addition of thioacetic acid to methacrylamides with chiral auxiliaries

Tetrahedron Asymmetry

Volumn 16, Issue 6, 2005, Pages 1215-1220

  Kim, Byung Hyun ^a   Lee, Hee Bong ^a   Hwang, Jae Kwang ^a   Kim, Young Gyu ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

1 (3' ACETYLTHIO 2' METHYLPROPANOYL)PROLINE; 1 (3' ACETYLTHIO 2' METHYLPROPANOYL)PROLINE METHYL ESTER; 1 (3' ACETYLTHIO 2' METHYLPROPANOYL)PROLINE PHENYL ESTER; 1 METHACRYLOYL 2 (BENZYLAMINOMETHYL)PYRROLIDINE; 1 METHACRYLOYL 2 (DIETHYLAMINOMETHYL)PYRROLIDINE; 1 METHACRYLOYL 2,5 BIS(METHOXYMETHYL)PYRROLIDINE; 1 METHACRYLOYL 2,5 DIMETHYLPYRROLIDINE; 1 METHACRYLOYLPROLINE; 1 METHACRYLOYLPROLINE METHYL ESTER; 1 METHACRYLOYLPROLINE PHENYL ESTER; 3 MERCAPTO 2 METHYLPROPANOIC ACID; ACETYLCAPTOPRIL; ACETYLCAPTOPRIL METHYL ESTER; ACETYLCAPTOPRIL PHENYL ESTER; AMIDE; BIS(METHOXYMETHYL)PYRROLIDINE; CAPTOPRIL; METHACRYLIC ACID DERIVATIVE; N METHACRYLOYL N,N BIS(PHENYLETHYL)AMINE; N TERT BUTYLOXYCARBONYLBIS(HYDROXYMETHYL)PYRROLIDINE; PROPIONIC ACID DERIVATIVE; PYRROLIDINE DERIVATIVE; THIOACETIC ACID; UNCLASSIFIED DRUG;

ACIDITY; ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; CYCLIZATION; DEMETHYLATION; DRUG CONJUGATION; DRUG SYNTHESIS; HYDROLYSIS; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; SUBSTITUTION REACTION; TRANS ISOMER;

EID: 14944354831     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.01.037     Document Type: Article

References (33)

1. R.B. Silverman The Organic Chemistry of Drug Design and Drug Action 1992 Academic San Diego pp 162-170
2. H. Kugita, H. Inoue, M. Ikezaki, M. Konda, and S. Takeo Chem. Pharm. Bull. 19 1971 595 602
3. T.-C. Tseng, and M.-J. Wu Tetrahedron: Asymmetry 6 1995 1633 1640
4. O. Miyata, T. Shinada, I. Ninomiya, and T. Naito Tetrahedron Lett. 32 1991 3519 3522
5. W.-J. Tsai, Y.-T. Lin, and B.-J. Uang Tetrahedron: Asymmetry 5 1994 1195 1198
6. M.-J. Wu, C.-C. Wu, and T.-C. Tseng J. Org. Chem. 59 1994 7188 7189
7. O. Miyata, T. Shinada, N. Kawakami, K. Taji, I. Ninomiya, T. Naito, T. Date, and K. Okamura Chem. Pharm. Bull. 40 1992 2579 2581
8. P. Perlmutter Conjugate Addition Reactions in Organic Synthesis 1992 Pergamon Oxford
9. M. Kanai, and M. Shibasaki Asymmetric Michael Reactions I. Ojima Catalytic Asymmetric Synthesis 2nd ed. 2000 VCH New York 569 592
10. M.P. Sibi, and S. Manyem Tetrahedron 56 2000 8033 8061
11. Y.S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, and M. Shibasaki J. Am. Chem. Soc. 122 2000 6506 6507
12. S.-G. Kim, and K.H. Ahn Tetrahedron Lett. 42 2001 4175 4177
13. T. Suzuki, and T. Torii Tetrahedron: Asymmetry 12 2001 1077 1081
14. N.A. Paras, and D.W.C. MacMillan J. Am. Chem. Soc. 124 2002 7894 7895
15. K. Nishimura, and K. Tomioka J. Org. Chem. 67 2002 431 434
16. J.H. Smitrovich, G.N. Boice, C. Qu, L. DiMichele, T.D. Nelson, M.A. Huffman, J. Murry, J. McNamara, and P.J. Reider Org. Lett. 4 2002 1963 1966
17. L. Keller, C. Camara, A. Pinheiro, F. Dumas, and J. d'Angelo Tetrahedron Lett. 42 2001 381 383
18. N. Prabagaran, and G. Sundararajan Tetrahedron: Asymmetry 13 2002 1053 1058
19. F. Effenberger, and H. Isak Chem. Ber. 122 1989 553 559
20. For a review see: J.K. Whitesell Chem. Rev. 89 1989 1581 1590
21. T.J. Donohoe, C.A. Stevenson, M. Helliwell, R. Irshad, and T. Ladduwahetty Tetrahedron: Asymmetry 10 1999 1315 1322
22. Y. Kawanami, I. Fujita, Y. Taniguchi, T. Katsuki, and M. Yamaguchi Chem. Lett. 1987 2021 2024
23. V. Gouverneur, and L. Ghosez Tetrahedron Lett. 32 1991 5349 5352
24. Y. Kawanami, T. Katsuki, and M. Yamaguchi Bull. Chem. Soc. Jpn. 60 1987 4190 4192
25. O. Kitagawa, T. Hanano, N. Kikuchi, and T. Taguchi Tetrahedron Lett. 34 1993 2165 2168
26. K. Fuji, M. Node, Y. Naniwa, and T. Kawabata Tetrahedron Lett. 31 1990 3175 3178
27. S. Ikegami, H. Uchiyama, T. Hayama, T. Katsuki, and M. Yamaguchi Tetrahedron 44 1988 5333 5342
28. M. Enomoto, Y. Ito, T. Katsuki, and M. Yamaguchi Tetrahedron Lett. 26 1985 1343 1344
29. B. Giese, U. Hoffmann, M. Roth, A. Velt, C. Wyss, M. Zehnder, and H. Zipse Tetrahedron Lett. 34 1993 2445 2448
30. N.A. Porter, D.M. Scott, I.J. Rosenstein, B. Giese, A. Veit, and H.G. Zeitz J. Am. Chem. Soc. 113 1991 1791 1799
31. R.H. Schlessinger, and E.J. Iwanowicz Tetrahedron Lett. 28 1987 2083 2086
32. W.D. Gurowitz, and M.A. Joseph J. Org. Chem. 32 1967 3289 3292
33. N.A. Sasaki, and I. Sagnard Tetrahedron 50 1994 7093 7108