Novel anti-β-functionalized γ,δ-unsaturated amino acids via a thio-Claisen rearrangement

Zhihua Liu; Hongchang Qu; Xuyuan Gu; Kwang Soo Lee; Bryan Grossman; Vlad K. Kumirov; Victor J. Hruby

doi:10.1016/j.tetlet.2010.04.102

Novel anti-β-functionalized γ,δ-unsaturated amino acids via a thio-Claisen rearrangement

Zhihua Liu, Hongchang Qu, Xuyuan Gu, Kwang Soo Lee, Bryan Grossman, Vlad K. Kumirov, Victor J. Hruby

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

14 Scopus citations

Abstract

A significantly improved thio-Claisen rearrangement method was developed for preparing anti-β-functionalized γ,δ-unsaturated amino acids, which are extremely useful nonproteinogenic amino acids used in chemistry and biology research. The mild reaction condition successfully introduced base labile functional groups into the amino acids with excellent anti/syn selectivities.

Original language	English (US)
Pages (from-to)	3518-3520
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	27
DOIs	https://doi.org/10.1016/j.tetlet.2010.04.102
State	Published - Jul 7 2010
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Novel anti-β-functionalized γ,δ-unsaturated amino acids via a thio-Claisen rearrangement",

abstract = "A significantly improved thio-Claisen rearrangement method was developed for preparing anti-β-functionalized γ,δ-unsaturated amino acids, which are extremely useful nonproteinogenic amino acids used in chemistry and biology research. The mild reaction condition successfully introduced base labile functional groups into the amino acids with excellent anti/syn selectivities.",

author = "Zhihua Liu and Hongchang Qu and Xuyuan Gu and Lee, {Kwang Soo} and Bryan Grossman and Kumirov, {Vlad K.} and Hruby, {Victor J.}",

note = "Funding Information: This work was supported by US Public Health Service Grants DK 17420 and the National Institute of Drug Abuse DA 06284 , DA 13449 . We also thank Professor Richard Glass (the University of Arizona) for useful discussions. ",

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doi = "10.1016/j.tetlet.2010.04.102",

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T1 - Novel anti-β-functionalized γ,δ-unsaturated amino acids via a thio-Claisen rearrangement

AU - Liu, Zhihua

AU - Qu, Hongchang

AU - Gu, Xuyuan

AU - Lee, Kwang Soo

AU - Grossman, Bryan

AU - Kumirov, Vlad K.

AU - Hruby, Victor J.

N1 - Funding Information: This work was supported by US Public Health Service Grants DK 17420 and the National Institute of Drug Abuse DA 06284 , DA 13449 . We also thank Professor Richard Glass (the University of Arizona) for useful discussions.

PY - 2010/7/7

Y1 - 2010/7/7

N2 - A significantly improved thio-Claisen rearrangement method was developed for preparing anti-β-functionalized γ,δ-unsaturated amino acids, which are extremely useful nonproteinogenic amino acids used in chemistry and biology research. The mild reaction condition successfully introduced base labile functional groups into the amino acids with excellent anti/syn selectivities.

AB - A significantly improved thio-Claisen rearrangement method was developed for preparing anti-β-functionalized γ,δ-unsaturated amino acids, which are extremely useful nonproteinogenic amino acids used in chemistry and biology research. The mild reaction condition successfully introduced base labile functional groups into the amino acids with excellent anti/syn selectivities.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Novel anti-β-functionalized γ,δ-unsaturated amino acids via a thio-Claisen rearrangement

Abstract

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