Stereoselective Control of Planar α-Dimethylsulfonium Benzyl Carbanions. Synthesis of Optically Pure trans-Aziridines

(R)-N-Sulfinylimine and (S)-N-sulfinylimine react with the ylide derived from (S)-dimethyl-[2-(p-toluenesulfinyl)phenyl]sulfonium salt, affording trans-2,3-disubstituted aziridines. A complete trans selectivity in low facial diastereoselectivity is observed when the configuration at the sulfur atoms...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-06, Vol.74 (11), p.4217-4224
Main Authors: Arroyo, Yolanda, Meana, Ángela, Rodríguez, J. Félix, Sanz-Tejedor, M. Ascensión, Alonso, Inés, García Ruano, José L
Format: Article
Language:English
Subjects:
Anions
Aziridines - chemical synthesis
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Imines - chemistry
Organic chemistry
Preparations and properties
Stereoisomerism
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Summary:(R)-N-Sulfinylimine and (S)-N-sulfinylimine react with the ylide derived from (S)-dimethyl-[2-(p-toluenesulfinyl)phenyl]sulfonium salt, affording trans-2,3-disubstituted aziridines. A complete trans selectivity in low facial diastereoselectivity is observed when the configuration at the sulfur atoms of the reagents is the same. Otherwise, when their configurations are different, the reaction evolved with total facial diastereoselectivity and the cis/trans ratio ranged between 1/4.2 and 1/9. Theoretical calculations indicate the reaction proceeds mainly by evolution of a planar free carbanion. The relative stability of the transition states predicts a trans/cis ratio that is in excellent agreement with the experimental results.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo900381b