1428366-50-0Relevant articles and documents
Design, synthesis, and applications of chiral N-2-phenyl-2-propyl sulfinyl imines for group-assisted purification (GAP) asymmetric synthesis
Pindi, Suresh,Wu, Jianbin,Li, Guigen
, p. 4006 - 4012 (2013/06/27)
A new chiral (Rs)-2-phenyl-2-propyl sulfinamide has been designed and synthesized; its derived aldimines and ketimines have been applied for asymmetric addition reaction with allylmagnesium bromide. The reaction was conveniently performed at room temperature to give a series of homoallylic amines in high yields (up to quant) and diastereoselectivity (up to >99% de). The pure products were obtained by relying on group-assisted purification (GAP) chemistry to avoid traditional purification methods of column chromatography or recrystallization. The conversion of disulfide to (Rs)-thiosulfinate which contains a newly generated polar group was also confirmed to be of the GAP chemistry in which washing crude product can generate pure enantiomer. The absolute stereochemistry has been determined by X-ray analysis.