Enantioselective synthesis of anti-β-substituted γ,δ- unsaturated amino acids: A highly selective asymmetric thio-Claisen rearrangement

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

doi:10.1021/ol801657q

Enantioselective synthesis of anti-β-substituted γ,δ- unsaturated amino acids: A highly selective asymmetric thio-Claisen rearrangement

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

Chemistry and Biochemistry

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

28 Scopus citations

Abstract

(Chemical Equation Presented) A novel synthesis of optically active anti-β-substituted γ,δ-unsaturated amino acids via a thio-Claisen rearrangement has been achieved. A 2,5-diphenylpyrrolidine was used as a (C₂-symmetric chiral auxiliary to control the stereochemistry, giving good yields and excellent diastereoselectivities and enantioselectivities.

Original language	English (US)
Pages (from-to)	4105-4108
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	18
DOIs	https://doi.org/10.1021/ol801657q
State	Published - 2008

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Enantioselective synthesis of anti-β-substituted γ,δ- unsaturated amino acids: A highly selective asymmetric thio-Claisen rearrangement",

abstract = "(Chemical Equation Presented) A novel synthesis of optically active anti-β-substituted γ,δ-unsaturated amino acids via a thio-Claisen rearrangement has been achieved. A 2,5-diphenylpyrrolidine was used as a (C2-symmetric chiral auxiliary to control the stereochemistry, giving good yields and excellent diastereoselectivities and enantioselectivities.",

author = "Zhihua Liu and Hongchang Qu and Xuyuan Gu and Min, {Byoung J.} and Joel Nyberg and Hruby, {Victor J.}",

year = "2008",

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T1 - Enantioselective synthesis of anti-β-substituted γ,δ- unsaturated amino acids

T2 - A highly selective asymmetric thio-Claisen rearrangement

AU - Liu, Zhihua

AU - Qu, Hongchang

AU - Gu, Xuyuan

AU - Min, Byoung J.

AU - Nyberg, Joel

AU - Hruby, Victor J.

PY - 2008

Y1 - 2008

N2 - (Chemical Equation Presented) A novel synthesis of optically active anti-β-substituted γ,δ-unsaturated amino acids via a thio-Claisen rearrangement has been achieved. A 2,5-diphenylpyrrolidine was used as a (C2-symmetric chiral auxiliary to control the stereochemistry, giving good yields and excellent diastereoselectivities and enantioselectivities.

AB - (Chemical Equation Presented) A novel synthesis of optically active anti-β-substituted γ,δ-unsaturated amino acids via a thio-Claisen rearrangement has been achieved. A 2,5-diphenylpyrrolidine was used as a (C2-symmetric chiral auxiliary to control the stereochemistry, giving good yields and excellent diastereoselectivities and enantioselectivities.

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JF - Organic Letters

SN - 1523-7060

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ER -

Enantioselective synthesis of anti-β-substituted γ,δ- unsaturated amino acids: A highly selective asymmetric thio-Claisen rearrangement

Abstract

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