Delineating origins of stereocontrol in asymmetric Pd-catalyzed α-hydroxylation of 1, 3-ketoesters

…, HS Rzepa, AJP White, D Billen, KK Hii

Index: Smith, Alexander M. R.; Rzepa, Henry S.; White, Andrew J. P.; Billen, Denis; Hii, King Kuok Journal of Organic Chemistry, 2010 , vol. 75, # 9 p. 3085 - 3096

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Citation Number: 51

Abstract

Systematic studies of reaction conditions and subsequent optimization led to the identification of important parameters for stereoselectivity in the asymmetric α-hydroxylation reaction of 1, 3-ketoesters. Enantioselectivities of up to 98% can be achieved for cyclic substrates and 88% for acyclic ketoesters. Subsequently, the combination of cyclic/acyclic ketoester, catalyst, and oxidant was found to have a profound effect on reaction rates and ...