A biocatalytic route to P-chirogenic compounds by lipase-catalyzed desymmetrization of a prochiral phosphine-borane.
Journal article, 2005
[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.
chemistry
Boranes
chemistry
Ligands
Phosphines
Molecular Structure
Lipase
Catalysis
Drug Design
chemistry
Stereoisomerism
Author
Daniel Wiktelius
University of Gothenburg
Magnus Johansson
Chalmers, Chemical and Biological Engineering, Organic and Analytical Chemistry
Kristina Luthman
University of Gothenburg
Nina Kann
Chalmers, Chemical and Biological Engineering, Organic and Analytical Chemistry
Published in
Organic Letters
1523-7060 (ISSN) 1523-7052 (eISSN)
Vol. 7 Issue 22 p. 4991-4994Categorizing
Subject Categories (SSIF 2011)
Medicinal Chemistry
Organic Chemistry
Identifiers
DOI
10.1021/ol0519893
PubMed
16235940