| Diastereoselective synthesis of polysubstituted tetrahydropyrans and thiacyclohexanes via indium trichloride mediated cyclizations. | |
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MedLine Citation:
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PMID: 11430091 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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Polysubstituted tetrahydropyrans and thiacyclohexanes were synthesized in high yields with excellent diastereoselectivities via indium trichloride mediated cyclizations between homoallyl alcohols and mercaptans with aldehydes. In the case of tetrahydropyran products, the stereochemistry of the product was found to be directly correlated with the geometry of the homoallyl alcohols; whereas the cross-cyclization of aldehydes with trans-homoallyl alcohols generated (up-down-up) 2,3,4-trisubstituted tetrahydropyran products exclusively, the reaction of aldehydes with cis-homoallyl alcohols provided mainly (up-up-up) 2,3,4-trisubstituted products. When a trisubstituted homoallyl alcohol was used, its cross-cyclization with aldehydes generated (up-down-up-down-up) pentasubstituted tetrahydropyran derivatives with simultaneous controlling of five stereogenic centers. On the other hand, a cyclization-decyclization equilibrium was observed in the formation of thiacyclohexanes. The reaction of both cis- and trans-homoallyl mercaptans with aldehydes provided the same major diastereomers. |
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Authors:
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X F Yang; J T Mague; C J Li |
Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 66 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2001 Feb |
Date Detail:
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Created Date: 2001-06-29 Completed Date: 2001-08-02 Revised Date: 2003-10-31 |
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: 739-47 Citation Subset: - |
Affiliation:
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Department of Chemistry, Tulane University, New Orleans, Louisiana 70118, USA. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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