Organic letters

Catalytic asymmetric addition of thiols to nitrosoalkenes leading to chiral non-racemic α-sulfenyl ketones

JM Hatcher, MC Kohler, DM Coltart

Index: Hatcher, John M.; Kohler, Mark C.; Coltart, Don M. Organic Letters, 2011 , vol. 13, # 15 p. 3810 - 3813

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Citation Number: 13

Abstract

The first asymmetric organocatalytic sulfenylation of in situ derived nitrosoalkenes leading to chiral nonracemic α-sulfenylated ketones is described. The transformation proceeds in an umpolung fashion, relative to enolate/azaenolate methods, and uses simple thiols, thereby obviating the need for electrophilic sulfur reagents.