Chiral phosphinamides: new catalysts for the asymmetric reduction of ketones by borane

Autor:	Barry N. Burns, Heather Tye, John R. Studley, N. Paul King, Martin Wills, Mark P. Gamble
Rok vydání:	1998
Předmět:	Reduction (complexity) chemistry.chemical_compound chemistry Hydroxy group Organic chemistry Reactivity (chemistry) Lewis acids and bases Borane Structural unit Redox Catalysis
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :1027-1038
ISSN:	1364-5463 0300-922X
Popis:	We have identified a new class of catalysts for the asymmetric reduction of prochiral ketones by borane. Key to the architecture of effective catalysts is an N–PO structural unit which may be part of a phosphinamide, phosphonamide or a related structure. Such catalysts are simple to prepare, are often crystalline solids and may be recovered from reduction reactions and reused. The catalysts act essentially as Lewis bases, serving to increase the reactivity of borane by electron donation. The incorporation of a hydroxy group into the catalyst provides an adjacent Lewis acid site upon reaction with borane and thus affords a superior catalyst capable of asymmetric inductions of up to 92% ee.
Databáze:	OpenAIRE
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