Synthesis of β- And γ-hydroxy α-amino acids via enzymatic kinetic resolution and cyanate-to-isocyanate rearrangement

Piotr Szczes̈niak; Agnieszka Październiok-Holewa; Urszula Klimczak; Sebastian Stecko

doi:10.1021/jo502026a

Synthesis of β- And γ-hydroxy α-amino acids via enzymatic kinetic resolution and cyanate-to-isocyanate rearrangement

Piotr Szczes̈niak
, Agnieszka Październiok-Holewa
, Urszula Klimczak
, Sebastian Stecko

Department of Organic Chemistry; Bioorganic Chemistry and Biotechnology (RCH/RCH2)

Institute of Organic Chemistry of the Polish Academy of Sciences

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

29 Citations (Scopus)

Abstract

A new strategy for stereoselective preparation of all four isomers of β- and γ-hydroxy α-amino acids is presented. The developed procedure is based on enzymatic kinetic resolution and cyanate-to-isocyanate rearrangement as key steps. Stereocontrol is achieved by proper choice of the starting hydroxyacid, the course of kinetic resolution, and the stereospecific sigmatropic rearrangement step, which proceeds with full chirality transfer.

Original language	English
Pages (from-to)	11700-11713
Number of pages	14
Journal	Journal of Organic Chemistry
Volume	79
Issue number	23
DOIs	https://doi.org/10.1021/jo502026a
Publication status	Published - 5 Dec 2014

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo502026a

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title = "Synthesis of β- And γ-hydroxy α-amino acids via enzymatic kinetic resolution and cyanate-to-isocyanate rearrangement",

abstract = "A new strategy for stereoselective preparation of all four isomers of β- and γ-hydroxy α-amino acids is presented. The developed procedure is based on enzymatic kinetic resolution and cyanate-to-isocyanate rearrangement as key steps. Stereocontrol is achieved by proper choice of the starting hydroxyacid, the course of kinetic resolution, and the stereospecific sigmatropic rearrangement step, which proceeds with full chirality transfer.",

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AU - Październiok-Holewa, Agnieszka

AU - Klimczak, Urszula

AU - Stecko, Sebastian

PY - 2014/12/5

Y1 - 2014/12/5

N2 - A new strategy for stereoselective preparation of all four isomers of β- and γ-hydroxy α-amino acids is presented. The developed procedure is based on enzymatic kinetic resolution and cyanate-to-isocyanate rearrangement as key steps. Stereocontrol is achieved by proper choice of the starting hydroxyacid, the course of kinetic resolution, and the stereospecific sigmatropic rearrangement step, which proceeds with full chirality transfer.

AB - A new strategy for stereoselective preparation of all four isomers of β- and γ-hydroxy α-amino acids is presented. The developed procedure is based on enzymatic kinetic resolution and cyanate-to-isocyanate rearrangement as key steps. Stereocontrol is achieved by proper choice of the starting hydroxyacid, the course of kinetic resolution, and the stereospecific sigmatropic rearrangement step, which proceeds with full chirality transfer.

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M3 - Article

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Synthesis of β- And γ-hydroxy α-amino acids via enzymatic kinetic resolution and cyanate-to-isocyanate rearrangement

Abstract

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