Synthesis of Chiral Nonracemic Tertiary α-Thio and α-Sulfonyl Acetic Esters via SN2 Reactions of Tertiary Mesylates

Abstract

Syntheses of enantioenriched sulfides and sulfones via substitution of tertiary mesylate with thiolate nucleophile with modest to excellent success.

Asymmetric synthesis of tertiary thiols and thioethers

“…For example, S N 2 displacement of a mesylate leaving group by thiophenol can be accomplished using α-hydroxy esters 2 (Scheme 1) [12]. …”

“…The efficiency of sulfonates as leaving groups has allowed the preparation of certain families of tertiary thiols and thioethers. For example, S N 2 displacement of a mesylate leaving group by thiophenol can be accomplished using α-hydroxy esters 2 ( Scheme 1 ) [ 12 ].…”