Gold(I)-Catalyzed Amination of Allylic Alcohols with Cyclic Ureas and Related Nucleophiles

Mukherjee, Paramita; Widenhoefer, Ross A

doi:10.1021/ol902923e

Abstract

A 1:1 mixture of [P(t-Bu)(2)-o-biphenyl]AuCl and AgSbF6 catalyzes the Intermolecular amination of allylic alcohols with 1-methylimidazolidin-2-one and related nucleophiles that, in the case of gamma-unsubstituted or gamma-methyl-substituted allylic alcohols, occurs with high gamma-regloselectivity and syn-stereoselectivity.

Type

Scholars@Duke

Ross A. Widenhoefer

Professor of Chemistry

Research in the Widenhoefer group is directed toward the development and mechanistic analysis of new organotransition metal-catalyzed transformations for application in the synthesis of functionalized organic molecules. In particular, our group has a long-standing interest in the functionalization of C–C multiple bonds with carbon and heteroatom nucleophiles catalyzed by electrophilic late transition metal complexes, with a recent focus on the synthetic and mechanistic aspect of gold(I) pi-acti

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