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Divergent Stereocontrol of Acid Catalyzed Intramolecular Aldol Reactions of 2,3,7-Triketoesters: Synthesis of Highly Functionalized Cyclopentanones.
MedLine Citation:
PMID:  22738671     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
The intramolecular acid catalyzed aldol cyclization of 2,3,7-triketoesters formed from ζ-keto-α-diazo-β-ketoesters provides highly functionalized cyclopentanones with good diastereoselectivity in high overall yields via kinetically controlled and stereodivergent catalytic processes. Lewis acid catalysis gives high selectivity for the 1,2-anti tetrasubstituted cyclopentanones, whereas Brønsted acid catalysis produces the corresponding 1,2-syn diastereomer.
Authors:
Phong Truong; Charles S Shanahan; Michael P Doyle
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-6-28
Journal Detail:
Title:  Organic letters     Volume:  -     ISSN:  1523-7052     ISO Abbreviation:  -     Publication Date:  2012 Jun 
Date Detail:
Created Date:  2012-6-28     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Department of Chemistry & Biochemistry, University of Maryland, College Park, Maryland 20742, United States.
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