title: Efficient, scalable asymmetric synthesis of an epoxy quinol via Noyori desymmetrization of a meso diketone.
abstract: Epoxy quinol 1a was prepared on a multi-gram scale by Noyori transfer hydrogenative desymmetrization of the readily available meso epoxy diketone 4. Although the intrinsic enantioselectivity for the desymmetrization was modest (82:18 er at 4% conversion), a highly enantiopure product (99.6:0.4 er) could be obtained in one operation in 44% yield via kinetic resolution of the minor enantiomer with long reaction times (48 h), or in 73% yield by combination with an enzymatic resolution of a 93:7 er mixture.
authors: Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, AR 72701, USA.
authors: David R
authors: DR
authors: Clay
authors: Ashley G
authors: AG
authors: Rosenberg
authors: Matthias C
authors: MC
authors: McIntosh