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 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.
Wiktelius
Daniel
D
Medicinal Chemistry, Department of Chemistry, Göteborg University, Sweden. daniel.wiktelius@chem.gu.se
Johansson
Magnus J
MJ
Luthman
Kristina
K
Kann
Nina
N
D001880:Boranes / Q000737:chemistry*; D002384:Catalysis; D015195:Drug Design; D005656:Fungal Proteins; D008024:Ligands; D008049:Lipase / Q000737:chemistry*; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
D001880:Boranes; D005656:Fungal Proteins; D008024:Ligands; D010720:Phosphines; D008049:Lipase; C431349:lipase B, Candida antarctica