Efficient trans-Selectivity in the Cyclocondensation of (S)-2-[2-(p-Tolylsulfinyl)phenyl]acetaldehyde with Activated Dienes Catalyzed by Yb(OTf)3

Reactions of (S)-2-[2-(p-tolylsulfinyl)phenyl]acetaldehyde 1 with Danishefsky's and related dienes took place in the presence of Yb(OTf)3 in a completely stereoselective manner, mediated by a remote sulfinyl group (1,5-asymmetric induction), to afford the corresponding 2,3-dihydro-4H-pyran-4-on...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-09, Vol.71 (20), p.7683-7689
Main Authors: García Ruano, José L, Fernández-Ibáñez, M. Ángeles, Maestro, M. Carmen
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Summary:Reactions of (S)-2-[2-(p-tolylsulfinyl)phenyl]acetaldehyde 1 with Danishefsky's and related dienes took place in the presence of Yb(OTf)3 in a completely stereoselective manner, mediated by a remote sulfinyl group (1,5-asymmetric induction), to afford the corresponding 2,3-dihydro-4H-pyran-4-ones. These reactions followed a stepwise mechanism, as was corroborated by isolation of the corresponding intermediates, with a high level of trans-selectivity for 4-methyl-substituted dienes. Treatment of the adducts with Raney Ni provided concomitant cleavage of the C−S bond and reduction of the conjugated carbonyl grouping.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo061128n