Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 8, Pages 4006-4012Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo400354r
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Funding
- NIH (Li, USA) [R21DA031860-01]
- Robert A. Welch Foundation (Li, USA) [D-1361]
- Jiangsu Rennovation Team Program (China)
- NSF [CHE-1048553]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1048553] Funding Source: National Science Foundation
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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 (R(s))-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.
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