Tetrahedron

Concise synthetic strategy toward cyclic α, α-disubstituted α-amino acids bearing a δ-nitrogen atom: chiral 1-substituted 4-aminopiperidine-4-carboxylic acids

M Oba, M Tanaka, Y Takano, H Suemune

Index: Oba, Makoto; Tanaka, Masakazu; Takano, Yukiko; Suemune, Hiroshi Tetrahedron, 2005 , vol. 61, # 3 p. 593 - 598

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Citation Number: 13

Abstract

A concise synthetic strategy toward cyclic α, α-disubstituted α-amino acids, 1-substituted 4- aminopiperidine-4-carboxylic acids have been developed. The synthetic route is a reductive amination of dimethyl bis (dioxolanemethyl) malonate with various amines, followed by Curtius rearrangement. This synthetic route is capable of synthesizing 4-aminopiperidine-4- carboxylic acids bearing a bulky substituent and optically active ones bearing a pendent ...