Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies of Alicyclic α-Amino Acids. IV. Conformational Analysis of Alicyclic α-Amino Acids and Stereochemistry of the Strecker and the Bucherer Reactions
YOSHIFUMI MAKITAKASHI MASUGIKOJI OZEKI
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1973 Volume 21 Issue 11 Pages 2466-2473

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Abstract
Conformational analysis of a pair of isomeric alicyclic α-amino acids was made by comparison of relative rates for alkaline hydrolysis of their ethyl esters. It was found that in a sharp contrast with the case of 2-norbornanone, employment of the Strecker and the Bucherer reactions in 2-bornanone resulted in the predominant formation of the corresponding amino acid possessing exo-amino and endo-carboxyl groups. On the basis of this finding, the stereochemical courses of the Strecker and the Bucherer reactions in the synthesis of alicyclic α-amino acid are also discussed.
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© The Pharmaceutical Society of Japan
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