| Efficient trans-selectivity in the cyclocondensation of (S)-2-[2-(p-tolylsulfinyl)phenyl]acetaldehyde with activated dienes catalyzed by Yb(OTf)3. | |
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MedLine Citation:
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PMID: 16995674 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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José L García Ruano; M Angeles Fernández-Ibáñez; M Carmen Maestro |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 71 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2006 Sep |
Date Detail:
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Created Date: 2006-09-25 Completed Date: 2007-07-25 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 7683-9 Citation Subset: - |
Affiliation:
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Departamento de Química Organica, Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain. joseluis.garcia.ruano@uam.es |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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