Asymmetric Copper-Catalyzed [2, 3]-Sigmatropic Rearrangements of Alkyl-and Aryl-Substituted Allyl Sulfides

DW McMillen, N Varga, BA Reed…

Index: McMillen, Douglas W.; Varga, Norbert; Reed, Beth Ann; King, Claudia Journal of Organic Chemistry, 2000 , vol. 65, # 8 p. 2532 - 2536

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Citation Number: 40

Abstract

The asymmetric copper-catalyzed generation and subsequent [2, 3]-sigmatropic rearrangement of sulfur ylides is strongly dependent on the structure of the starting allyl sulfide. A series of alkyl and aryl substituted allyl sulfides (2a-i) were reacted with ethyl diazoacetate in the presence of copper triflate (CuOTf) and a C 2-symmetric bis-oxazoline ligand (5a-c). The degree of asymmetric induction ranged from 2.8% for allyl methyl ...