title: Stereoselective alkylidenation of ketones with 2-(p-toluenesulfinyl)benzyl iodide: synthesis of enantiomerically pure trisubstituted epoxides.
abstract: Alkylidenation of arylmethyl, dialkyl, and cyclic ketones with 2-( p-toluenesulfinyl)benzyl iodide in the presence of NaN(SiMe3)2 takes place with a high or complete control of the facial selectivity at the carbonyl group (up to 98% de) and the carbanion (>98% de), respectively, yielding mixtures of only two optically pure trisubstituted epoxides ( E/Z ratio ranges between 2:1 and >50:1). Removal of the p-tolylsulfinyl group with t-BuLi provides the corresponding (E)-3-phenyl-2,2-disubstituted epoxides without affecting their optical purity.
authors.affiliation: Departamento de Química Orgánica (ETSII), Universidad de Valladolid, Valladolid, Spain. yarroyo@eis.uva.es
authors.forename: Yolanda
authors.initials: Y
authors.lastname: Arroyo
authors.forename: Angela
authors.initials: A
authors.lastname: Meana
authors.forename: M Ascensión
authors.initials: MA
authors.lastname: Sanz-Tejedor
authors.forename: José Luis García
authors.initials: JL
authors.lastname: Ruano