A new approach for construction of quarternary chiral centers: Preparation of α-branched serine derivatives

Heterocycles

Volumn 53, Issue 5, 2000, Pages 1011-1016

  Uno, Hidemitsu ^a   Kasahara, Ken Ichi ^a   Ono, Noboru ^a  

^a EHIME UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; OXAZOLONE; SERINE DERIVATIVE;

AMINO ACID ANALYSIS; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; OXIDATION REDUCTION REACTION; SYNTHESIS;

EID: 0034194829     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-00-8863     Document Type: Article

References (17)

1. R. M. Williams, "Synthesis of Optically Active α-Amino Acids" Pergamon Press, 1989, London.
2. T. Mukaiyama, Organic Reactions, 1982, 28, Chap. 3.
3. H. Uno, J. E. Baldwin, and A. T. Russell, J. Am. Chem. Soc., 1994, 116, 2139; H. Uno, J. E. Baldwin, I. Churcher, and A. T. Russell, Synlett, 1997, 390; H. Uno, N. Mizobe, Y. Yamaoka, and N. Ono, Heterocycles, 1998, 48, 635.
4. H. Uno, J. E. Baldwin, and A. T. Russell, J. Am. Chem. Soc., 1994, 116, 2139; H. Uno, J. E. Baldwin, I. Churcher, and A. T. Russell, Synlett, 1997, 390; H. Uno, N. Mizobe, Y. Yamaoka, and N. Ono, Heterocycles, 1998, 48, 635.
5. H. Uno, J. E. Baldwin, and A. T. Russell, J. Am. Chem. Soc., 1994, 116, 2139; H. Uno, J. E. Baldwin, I. Churcher, and A. T. Russell, Synlett, 1997, 390; H. Uno, N. Mizobe, Y. Yamaoka, and N. Ono, Heterocycles, 1998, 48, 635.
6. For other examples, see: S. Sano, X. -K. Liu, M. Takebayashi, Y. Kobayashi, K. Tabata, M. Shiro, and Y. Nagao, Tetrahedron Lett., 1995, 36, 4101; Y. Itoh, M. Sawamura, E. Shirakawa, K. Hayashizaki, and T. Hayashi, Tetrahedron Lett., 1988, 29, 235; D. Seebach and J. D. Aebi, Tetrahedron Lett., 1984, 25, 2545; U. Groth, Y. Chiang, and U. Schöllkopf, Liebigs Ann. Chem. 1982, 1756.
7. For other examples, see: S. Sano, X. -K. Liu, M. Takebayashi, Y. Kobayashi, K. Tabata, M. Shiro, and Y. Nagao, Tetrahedron Lett., 1995, 36, 4101; Y. Itoh, M. Sawamura, E. Shirakawa, K. Hayashizaki, and T. Hayashi, Tetrahedron Lett., 1988, 29, 235; D. Seebach and J. D. Aebi, Tetrahedron Lett., 1984, 25, 2545; U. Groth, Y. Chiang, and U. Schöllkopf, Liebigs Ann. Chem. 1982, 1756.
8. For other examples, see: S. Sano, X. -K. Liu, M. Takebayashi, Y. Kobayashi, K. Tabata, M. Shiro, and Y. Nagao, Tetrahedron Lett., 1995, 36, 4101; Y. Itoh, M. Sawamura, E. Shirakawa, K. Hayashizaki, and T. Hayashi, Tetrahedron Lett., 1988, 29, 235; D. Seebach and J. D. Aebi, Tetrahedron Lett., 1984, 25, 2545; U. Groth, Y. Chiang, and U. Schöllkopf, Liebigs Ann. Chem. 1982, 1756.
9. For other examples, see: S. Sano, X. -K. Liu, M. Takebayashi, Y. Kobayashi, K. Tabata, M. Shiro, and Y. Nagao, Tetrahedron Lett., 1995, 36, 4101; Y. Itoh, M. Sawamura, E. Shirakawa, K. Hayashizaki, and T. Hayashi, Tetrahedron Lett., 1988, 29, 235; D. Seebach and J. D. Aebi, Tetrahedron Lett., 1984, 25, 2545; U. Groth, Y. Chiang, and U. Schöllkopf, Liebigs Ann. Chem. 1982, 1756.
10. F. Zanardi, L. Battistini, G. Rassu, M. Corna, and G. Casiraghi, J. Chem. Soc., Perkin Trans. 1, 1995, 2471.
11. G. Casiraghi and G. Rassu, Synthesis, 1995, 607.
12. H. Uno, Y. Nishihara, N. Mizobe, and N. Ono, Bull. Chem. Soc. Jpn., 1999, 72, 1533.
13. Although osmylation was succesfully carried out in the presence of a nitro group, we could not achieve the reaction under various conditions, see: B. M. Trost, G. -H. Kuo, and T. Benneche, J. Am. Chem. Soc., 1988, 110, 621.
14. N. Ono, H. Miyake, R. Tamura, and A. Kaji, Tetrahedron Lett., 1981, 22, 1705.
15. 3 according to the modified procedure by G. Stork and T. Takahashi. "Yuukikagaku jikkenn no tebiki (Handbook for Organochemical Experiments)" T. Goto, T. Shiba, and T. Matsuura, Eds. Kagakudoujinn (Kyoto), 1990, Vol. 2, p 12.
16. 3 according to the modified procedure by G. Stork and T. Takahashi. "Yuukikagaku jikkenn no tebiki (Handbook for Organochemical Experiments)" T. Goto, T. Shiba, and T. Matsuura, Eds. Kagakudoujinn (Kyoto), 1990, Vol. 2, p 12.
17. M. Isobe, Y. Ichikawa, D. -L. Bai, and T. Goto, Tetrahedron, 1987, 43, 4767.