Diastereoselectivity Control in Formal Nucleophilic Substitution of Bromocyclopropanes with Oxygen-and Sulfur-Based Nucleophiles

…, AR Prosser, BK Alnasleh, J Smarker…

Index: Banning, Joseph E.; Prosser, Anthony R.; Alnasleh, Bassam K.; Smarker, Jason; Rubina, Marina; Rubin, Michael Journal of Organic Chemistry, 2011 , vol. 76, # 10 p. 3968 - 3986

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Citation Number: 27

Abstract

A diastereoconvergent formal nucleophilic substitution of bromocyclopropanes with oxygen- and sulfur-based nucleophiles is described. The reaction proceeds via in situ formation of a highly reactive cyclopropene intermediate and subsequent diastereoselective addition of a nucleophile across the strained C C bond. Three alternative means of controlling the diastereoselectivity of addition have been demonstrated:(1) thermodynamically driven ...