1029690-06-9Relevant academic research and scientific papers
Stereoselective alkylidenation of ketones with 2-(p-toluenesulfinyl)benzyl iodide: Synthesis of enantiomerically pure trisubstituted epoxides
Arroyo, Yolanda,Meana, Angela,Sanz-Tejedor, M. Ascension,Ruano, Jose Luis Garcia
, p. 2151 - 2154 (2008)
(Chemical Equation Presented) 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.
