Document Detail


Acid-promoted Prins cyclizations of enol ethers to form tetrahydropyrans.
MedLine Citation:
PMID:  12713308     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Trifluoroacetic acid efficiently catalyzes Prins cyclizations of enol ethers 8 to provide tetrahydropyrans 9 and 10. These tetrahydropyrans are isolated with combined yields of 42-85% and stereoselectivities at C(4) ranging from 95:5 to 50:50 depending on the nature of the substituent R. Unique byproducts of these cyclizations that reveal the presence of underlying equilibria have been isolated and identified. [reaction: see text]
Authors:
David J Hart; Chad E Bennett
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Organic letters     Volume:  5     ISSN:  1523-7060     ISO Abbreviation:  Org. Lett.     Publication Date:  2003 May 
Date Detail:
Created Date:  2003-04-25     Completed Date:  2003-08-08     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1499-502     Citation Subset:  IM    
Affiliation:
Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, OH 43210, USA. hart@chemistry.ohio-state.edu
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MeSH Terms
Descriptor/Qualifier:
Catalysis
Cyclization
Ethers / chemistry*
Pyrans / chemical synthesis*
Stereoisomerism
Trifluoroacetic Acid / chemistry*
Chemical
Reg. No./Substance:
0/Ethers; 0/Pyrans; 76-05-1/Trifluoroacetic Acid

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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