A Biocatalytic Route to P-Chirogenic Compounds by Lipase-Catalyzed Desymmetrization of a Prochiral Phosphine−Borane

Daniel Wiktelius, Magnus J. Johansson, Kristina Luthman, Nina Kann

Organic Letters · 2005 · 53 citations · 17 references

Abstract

[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.

References

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