Journal
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
Volume 188, Issue 4, Pages 275-286Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/10426507.2012.729116
Keywords
Sulfenates; alkylation; diastereoselection; sulfur nucleophile
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Sulfenates, the conjugate bases of sulfenic acids are nucleophilic species that can be alkylated at sulfur to create sulfoxides. Sulfenates are generally not isolable, but must be generated and functionalized in solution. In this report, we summarize accomplishments toward the liberation of 1-alkenesulfenate anions and also the first general method for the release of alkane- and arenesulfenates. As prochiral entities, there is also potential for their stereoselective alkylation. As such, a protected cysteinesulfenate has been generated and alkylated at sulfur with dr's as high as 95:5. Also, when there is stereogenicity in the electrophile, diastereoselective alkylation of simple arenesulfenates occurs with dr's approaching and exceeding 9:1.
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