Rhodium-Catalyzed Asymmetric Cyclodimerization of Oxabenzonorbornadienes and Azabenzonorbornadienes:  Scope and Limitations

Cationic rhodium(I)-catalyzed cyclodimerization of oxabenzonorbornadienes produced naphtho[1,2-b]furan ring systems in a single step with excellent yields and excellent enantioselectivities. The effect of various Rh(I) catalysts, Ag(I) salts, solvents, and phosphine ligands on the yield and enantios...

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Bibliographic Details
Published in:Journal of organic chemistry 2007-10, Vol.72 (21), p.7849-7857
Main Authors: Allen, Anna, Le Marquand, Paul, Burton, Ryan, Villeneuve, Karine, Tam, William
Format: Article
Language:English
Subjects:
Catalysis
Catalysts: preparations and properties
Chemistry
Exact sciences and technology
General and physical chemistry
Organic chemistry
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:Cationic rhodium(I)-catalyzed cyclodimerization of oxabenzonorbornadienes produced naphtho[1,2-b]furan ring systems in a single step with excellent yields and excellent enantioselectivities. The effect of various Rh(I) catalysts, Ag(I) salts, solvents, and phosphine ligands on the yield and enantioselectivity of the reaction was investigated, and the scope and limitations of this reaction with various oxabicyclic alkenes were studied. Similar results were obtained with the azabenzonorbornadiene analogues, providing the corresponding cyclodimerization products in excellent yields and excellent enantioselectivities.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo7012884