Stereoselective One-Pot Synthesis of β-Alkylsulfide Enol Esters. Base-triggered Rearrangement under Mild Conditions

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

ROYAL SOC CHEMISTRY

Lugar: CAMBRIDGE; Año: 2014 vol. 12 p. 6516 - 6516

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 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.