Synthesis of anti-β-substituted γ,δ-unsaturated amino acids via Eschenmoser-Claisen rearrangement

Hongchang Qu; Xuyuan Gu; Byoung J. Min; Zhihua Liu; Victor J. Hruby

doi:10.1021/ol061414l

Synthesis of anti-β-substituted γ,δ-unsaturated amino acids via Eschenmoser-Claisen rearrangement

Hongchang Qu, Xuyuan Gu, Byoung J. Min, Zhihua Liu, Victor J. Hruby

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

21 Scopus citations

Abstract

(Chemical Equation Presented) Anti-β-substituted γ,δ- unsaturated amino acids have been synthesized via a novel design of the Eschenmoser-Claisen rearrangement. The rearrangement gives good isolated yields and excellent diastereoselectivity due to (Z)-N,O-ketene acetal formation and the pseudochairlike conformations of the reaction intermediates. Upon reductive hydrolysis, important novel amino acids and amino alcohols were synthesized for the first time via this methodology.

Original language	English (US)
Pages (from-to)	4215-4218
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	19
DOIs	https://doi.org/10.1021/ol061414l
State	Published - Sep 14 2006

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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AU - Qu, Hongchang

AU - Gu, Xuyuan

AU - Min, Byoung J.

AU - Liu, Zhihua

AU - Hruby, Victor J.

PY - 2006/9/14

Y1 - 2006/9/14

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AB - (Chemical Equation Presented) Anti-β-substituted γ,δ- unsaturated amino acids have been synthesized via a novel design of the Eschenmoser-Claisen rearrangement. The rearrangement gives good isolated yields and excellent diastereoselectivity due to (Z)-N,O-ketene acetal formation and the pseudochairlike conformations of the reaction intermediates. Upon reductive hydrolysis, important novel amino acids and amino alcohols were synthesized for the first time via this methodology.

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Synthesis of anti-β-substituted γ,δ-unsaturated amino acids via Eschenmoser-Claisen rearrangement

Abstract

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