Diastereoselective Alkylations of a Protected Cysteinesulfenate
journal contributionposted on 04.09.2009, 00:00 by Adrian L. Schwan, Marcus J. Verdu, Suneel P. Singh, Jennifer S. O’Donnell, Amir Nasser Ahmadi
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.