Synthesis of menthyl sulfinate and sulfoxides on solid phase

Recent Developments in the Synthesis and Utilization of Chiral Sulfoxides

“…Hanquet and Solladié recently reported the support-bound menthyl sulfinate and sulfoxides as a first step toward applying their well-established sulfoxide chemistry to solid-phase synthesis. , Racemic p -hydroxyphenyl sulfoxide 354 and the diastereomeric mixture of menthyl sulfinate esters 355 were attached to the Wang resin via a Mitsonubu reaction, affording methyl sulfoxide and menthyl sulfinate linkers 356 and 357 (Scheme ). Condensation of Grignard reagents on 357 afforded polymer-supported aryl sulfoxides, while the condensation of potassium or lithium enolates afforded β-keto sulfoxides in moderate yields.…”

Recent developments in chiral non-racemic sulfinyl group chemistry in asymmetric synthesis

“…The route to asymmetric solidphase synthesis using optically active sulfoxides is opened since enantiomerically enriched polymer-bound β-ketosulfoxides are available from enantiomerically pure Wang-supported palkoxyphenylmenthyl-sulfinate. 67 Toru et al have also used optically active sulfoxides as linkers and chiral auxiliaries in an asymmetric conjugate addition of polymer-supported enantiomerically enriched β-(trimethylsilyl)ethyl sulfoxide to cinnamate derivatives. Thermal treatment or reaction with TBAF liberates chiral non-racemic 3-phenyl-5-trimethylsilylpent-4-enoates or 3-phenylpent-4-enoates respectively with high enantioselectivity (ee 90%).…”