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

Katedra Chemii Organicznej, Bioorganicznej i Biotechnologii (RCH/RCH2)

Institute of Organic Chemistry of the Polish Academy of Sciences

Wyniki badań: Wkład do czasopisma › Artykuł › recenzja

29 Cytowania z bazy Scopus

Abstrakt

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.

Język oryginału	angielski
Strony (od–do)	11700-11713
Liczba stron	14
Czasopismo	Journal of Organic Chemistry
Tom	79
Numer wydania	23
Identyfikatory DOI	https://doi.org/10.1021/jo502026a
Status publikacji	Opublikowano - 5 gru 2014

Obszary tematyczne ASJC Scopus

Chemia organiczna

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10.1021/jo502026a

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Cytowanie

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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.",

author = "Piotr Szcze{\"s}niak and Agnieszka Pa{\'z}dzierniok-Holewa and Urszula Klimczak and Sebastian Stecko",

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T1 - Synthesis of β- And γ-hydroxy α-amino acids via enzymatic kinetic resolution and cyanate-to-isocyanate rearrangement

AU - Szczes̈niak, Piotr

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.

UR - https://www.scopus.com/pages/publications/84916213098

U2 - 10.1021/jo502026a

DO - 10.1021/jo502026a

M3 - Article

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AN - SCOPUS:84916213098

SN - 0022-3263

VL - 79

SP - 11700

EP - 11713

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 23

ER -

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

Abstrakt

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