Synthesis of diastereomerically and enantiomerically pure 2, 3-disubstituted tetrahydrofurans using a sulfoxonium ylide

JM Schomaker, VR Pulgam…

Index: Schomaker, Jennifer M.; Pulgam, Veera Reddy; Borhan, Babak Journal of the American Chemical Society, 2004 , vol. 126, # 42 p. 13600 - 13601

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Citation Number: 61

Abstract

Nucleophilic substitution reactions of 2, 3-epoxy alcohols, easily prepared via Sharpless asymmetric epoxidation chemistry, offer access to a wide variety of enantiomerically pure compounds. In this communication, we describe the use of a Payne rearrangement to control regioselectivity in the ring-opening of a series of 2, 3-epoxy alcohols with dimethylsulfoxonium methylide to yield diastereomerically and/or enantiomerically pure ...

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