Stereoselective Addition of α-Methylsulfenyl Benzyl Carbanions to N-Sulfinylketimines: Asymmetric Synthesis of α,α-Dibranched β-Sulfanyl Amines

(R)- and (S)-N-sulfinylketimines react with the ortho-sulfinyl benzyl carbanion derived from (S)-1 affording epimeric mixtures at the benzylic carbon of α,α-dibranched β-sulfanyl amines. The N-sulfinyl group completely controls the configuration at the quaternary carbon bonded to the nitrogen, where...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-01, Vol.74 (2), p.764-772
Main Authors: Arroyo, Yolanda, Meana, Ángela, Sanz-Tejedor, M. Ascensión, Alonso, Inés, Ruano, José L. García
Format: Article
Language:English
Subjects:
Amines - chemical synthesis
Amines - chemistry
Imines - chemistry
Magnetic Resonance Spectroscopy
Quantum Theory
Stereoisomerism
Substrate Specificity
Sulfenic Acids - chemistry
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Summary:(R)- and (S)-N-sulfinylketimines react with the ortho-sulfinyl benzyl carbanion derived from (S)-1 affording epimeric mixtures at the benzylic carbon of α,α-dibranched β-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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo802200f