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

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

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 el...

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Veröffentlicht in:Organic letters 2011-08, Vol.13 (15), p.3810-3813
Hauptverfasser: Hatcher, John M, Kohler, Mark C, Coltart, Don M
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2012633