Design, Synthesis, and Applications of Chiral <i>N</i>‑2-Phenyl-2-propyl Sulfinyl Imines for Group-Assisted
Purification (GAP) Asymmetric Synthesis
- Publication date
- Publisher
Abstract
A new
chiral (<i>R<sub>s</sub></i>)-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 (<i>R</i><sub><i>s</i></sub>)-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