期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 2, 页码 764-772出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo802200f
关键词
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资金
- Spanish Government [CTQ2006-06741]
- JCYL [VA-085A08]
(R)- and (S)-N-sulfinylketimines react with the ortho-sulfinyl benzyl carbanion derived from (S)-1 affording epimeric mixtures at the benzylic carbon of alpha,alpha-dibranched beta-sulfanyl amines. The N-sulfinyl group completely controls the configuration at the quaternary carbon bonded to the nitrogen, whereas the C-sulfinyl group is responsible for the level of asymmetric induction. High stereoselectivity can be achieved when the configuration at the sulfur atoms of the reagents are opposite (matched pair). After a two-step desulfinylation process, this reaction provides a procedure for synthesizing diastereomerically pure syn-1,2-sulfanyl amines containing a chiral quaternary carbon adjacent to nitrogen.
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