Amino Acids and Peptides. XXIX.1) A New Efficient Asymmetric Synthesis of a-Amino Acid Derivatives with Recycle of a Chiral Reagent—Asymmetric Alkylation of a Chiral Schiff Base from Glycine2)

Chemical and Pharmaceutical Bulletin

Volumn 26, Issue 3, 1978, Pages 803-808

  Oguri, Tomei ^a   Kawai, Nobutaka ^a   Shioiri, Takayuki ^a   Shun Ichi, Yamada ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

alkylation; amino acid; asymmetric synthesis; carbanion; chiral reagent; lithium diisopropylamide; proliferation of the asymmetry; Schiff base; pinene

Indexed keywords

AMINO ACID DERIVATIVE;

DRUG ANALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROMETRY; METHODOLOGY; POLARIMETRY; THEORETICAL STUDY;

EID: 0017876845     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.26.803     Document Type: Article

References (14)

1. Part XXVIII: T. Oguri, T. Shioiri, and S. Yamada, Chem. Pharm. Bull. (Tokyo), 25, 2287 (1977).
2. A part of this work was presented at the 96th Annual Meeting of the Pharmaceutical Society of Japan, Osaka, April, 1975, Abstracts of Papers, II, p. 4; Preliminary Communication, S. Yamada, T. Oguri, and T. Shioiri, Chem. Commun., 1976, 136.
3. Location: 7-3-1, Hongo, Bunkyo-ku, Tokyo 113, Japan; a) Present address: Faculty of Pharmaceutical Sciences, Nagoya City University, 3–1, Tanahe-dori, Mizuho-ku, Nagoya 467, Japan.
4. Cf., S. Yamada, T. Oguri, and T. Shioiri, Chem. Commun., 1972, 623; T. Oguri, T. Shioiri, and S. Yamada, Chem. Pharm. Bull. (Tokyo), 23, 167 (1975).
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9. A.W. Schrecker and J.L. Hartwell, J. Am. Chem. Soc., 79, 3827 (1957).
10. G.H. Timms and E. Wildsmith, Tetrahedron Lett., 1971, 195.
11. D+45.9°’ (neat).
12. G.W. Anderson and R.M. Callahan, J. Am. Chem. Soc., 82, 3359 (1960).
13. R.W. Roeske (Chem. and Ind., 1959, 1121) describes this hydrochloride decomposes without melting.
14. A. Nakamoto, M. Aburatani, and M. Inagaki, J. Med. Chem., 14, 1021 (1971).