Diastereoselective alkylations of a protected cysteinesulfenate.

ABSTRACT

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 8317 to 955. An internally complexed lithium counterion is proposed to account for the stereoselectivity.