Design, synthesis, and applications of chiral N-2-phenyl-2-propyl sulfinyl imines for group-assisted purification (GAP) asymmetric synthesis

Suresh Pindi, Jianbin Wu, Guigen Li

Research output: Contribution to journalArticle

33 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)4006-4012
Number of pages7
JournalJournal of Organic Chemistry
Volume78
Issue number8
DOIs
StatePublished - Apr 19 2013

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