A biocatalytic route to P-chirogenic compounds by lipase-catalyzed desymmetrization of a prochiral phosphine-borane.

[reaction: see text] Available methods for synthesis of P-chirogenic compounds are limited. We set out to find biocatalytical means to introduce asymmetry in a phosphine-borane. After screening different lipases, Candida antarctica lipase B was found to give excellent results in the desymmetrization...

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Bibliographic Details
Published in:Organic Letters
Main Authors: Wiktelius, Daniel, Johansson, Magnus, Luthman, Kristina, Kann, Nina
Language:unknown
Published: 2005
Subjects:
Medicinal Chemistry
Organic Chemistry
chemistry
Boranes
Ligands
Phosphines
Molecular Structure
Lipase
Catalysis
Drug Design
Stereoisomerism
Antarc*
Antarctica
Online Access:https://doi.org/10.1021/ol0519893
https://research.chalmers.se/en/publication/54833
Description
Summary:[reaction: see text] Available methods for synthesis of P-chirogenic compounds are limited. We set out to find biocatalytical means to introduce asymmetry in a phosphine-borane. After screening different lipases, Candida antarctica lipase B was found to give excellent results in the desymmetrization of prochiral phosphine-boranes. Both enantiomers can be obtained in up to >98% optical purity via acetylation or hydrolysis in processes that allow recycling of the substrates.

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