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Asymmetric Chemoenzymatic One-Pot Synthesis of α-Hydroxy Half-Esters.

ABSTRACT: A new chemoenzymatic one-pot strategy has been developed for the synthesis of α-hydroxy half-esters containing consecutive quaternary and tertiary stereocenters using asymmetric cascade catalysis. In this study, an asymmetric Ca²⁺-catalyzed [2,3]-Wittig rearrangement reaction was proven to be suitable for a combination with porcine liver esterase-mediated hydrolysis resulting in the enhanced enantiomeric purity of the obtained products in a one-pot synthesis compared to the stepwise method.

SUBMITTER: Murre A

PROVIDER: S-EPMC8359131 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

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Asymmetric Chemoenzymatic One-Pot Synthesis of α-Hydroxy Half-Esters.

Murre Aleksandra A Erkman Kristin K Järving Ivar I Kanger Tõnis T

ACS omega 20210728 31

A new chemoenzymatic one-pot strategy has been developed for the synthesis of α-hydroxy half-esters containing consecutive quaternary and tertiary stereocenters using asymmetric cascade catalysis. In this study, an asymmetric Ca<sup>2+</sup>-catalyzed [2,3]-Wittig rearrangement reaction was proven to be suitable for a combination with porcine liver esterase-mediated hydrolysis resulting in the enhanced enantiomeric purity of the obtained products in a one-pot synthesis compared to the stepwise m ...[more]

PMID: 34396014

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