Synthesis of β- and γ‑Hydroxy α‑Amino Acids via Enzymatic Kinetic Resolution and Cyanate-to-Isocyanate Rearrangement

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 hydroxy...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-12, Vol.79 (23), p.11700-11713
Main Authors: Szcześniak, Piotr, Październiok-Holewa, Agnieszka, Klimczak, Urszula, Stecko, Sebastian
Format: Article
Language:English
Subjects:
Amino Acids - chemical synthesis
Amino Acids - chemistry
Biochemical Phenomena
Cyanates - chemistry
Isocyanates - chemistry
Kinetics
Molecular Structure
Stereoisomerism
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo502026a