Tetrahedron letters

Stereocontrolled synthesis of α, α-disubstituted α-aminoaldehydes and α-aminoacids using a [3, 3] allylic trichloracetimidate rearrangement

H Imogaï, Y Petit, M Larchevêque

Index: Imogai, Hassan; Petit, Yves; Larcheveque, Marc Tetrahedron Letters, 1996 , vol. 37, # 15 p. 2573 - 2576

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Citation Number: 25

Abstract

Sigmatropic rearrangement of trichloracetimidates derived from syn monoprotected allylic diols 3 resulting from the condensation of vinylalanes or cuprates with α-alkoxyaldehydes afforded diastereomerically pure allylic amines 6. The oxidative cleavage of these amines allowed the access to α, α-disubstituted α-aminoacids in high enantiomeric purity.

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