1428365-94-9Relevant articles and documents
CHIRAL 2-ARYLPROPYL-2-SULFINAMIDE AND CHIRAL N-2-ARYLPROPYL-2-SULFINYLIMINES AND SYNTHESIS THEREOF
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Page/Page column, (2014/09/30)
Provided herein are novel chiral sulfinamide and imine compounds. Also provided herein are methods of synthesizing novel chiral sulfinamide and imine compounds comprising simplified purification methods when compared to prior methods. The novel chiral sulfinamide and imine compounds are useful, for example, in the synthesis of complex natural products and pharmaceutical important compounds.
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.
