Stereoselective one-pot synthesis of β-alkylsulfide enol esters. Base-triggered rearrangement under mild conditions

HEREDIA, ADRIÁN A.; SORIA-CASTRO, SILVIA; BOUCHET, LYDIA; OKSDATH MANSILLA, GABRIELA; PEÑÉÑORY, ALICIA B.; BARRIONUEVO, CECILIA A.; CAMINOS, DANIEL A.; BISOGNO, FABRICIO R.; ARGÜELLO, JUENA E.; PEÑÉÑORY, ALICIA B.

ROYAL SOC CHEMISTRY

Lugar: CAMBRIDGE; Año: 2014

stereoselective one-pot procedure was developed to prepare S-substituted (Z)-enol esters through a base-triggered rearrangement. This transition metal-free multicomponent approach can be performed under an air atmosphere at room temperature, tolerates a wide set of chemical functionalities and generally affords high isolated yields. The (Z)-selectivity arises from the [1,4]-S- to O-acyl migration.