Diastereoselective alkylations of a protected cysteinesulfenate.
To further understand stereoselection in the alkylation of sulfenate anions, a protected cysteinesulfenate was generated in THF solution at low temperature. Introduction of a reactive alkylating agent brings about a cysteinyl sulfoxide in 51-75% yield, with diastereomeric ratios at the sulfinyl group ranging from 83:17 to 95:5. An internally complexed lithium counterion is proposed to account for the stereoselectivity.
Schwan
Adrian L
AL
Department of Chemistry, University of Guelph, Guelph, Ontario, Canada, N1G 2W1. schwan@uoguelph.ca
Verdu
Marcus J
MJ
Singh
Suneel P
SP
O'Donnell
Jennifer S
JS
Ahmadi
Amir Nasser
AN