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Catalytic Asymmetric Addition of Thiols to Nitrosoalkenes Leading to Chiral Non-Racemic α-Sulfenyl Ketones

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journal contribution
posted on 2011-08-05, 00:00 authored by John M. Hatcher, Mark C. Kohler, Don M. Coltart
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.

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