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Chiral Oxazaborolidine−Aluminum Bromide Complexes Are Unusually Powerful and Effective Catalysts for Enantioselective Diels−Alder Reactions

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Duan Liu, Eda Canales, and E. J. Corey*

Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138

J. Am. Chem. Soc., 2007, 129 (6), pp 1498–1499

DOI: 10.1021/ja068637r

Publication Date (Web): January 19, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, corey@chemistry.harvard.edu

Abstract

Treatment of the chiral oxazaborolidine 1 with AlBr₃ generates the 1:1 complex 3, which is an even more potent Lewis acid catalyst than protonated 1 (i.e., 2) for enantioselective Diels−Alder reactions. Only 4 mol % of catalyst 3 is required to achieve yields and enantiomeric purities of 90% over a broad range of achiral dienes and dienophiles. The ligand from which 3 is derived can be recovered easily and with high efficiency. The method is illustrated by 22 examples.

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Published In Issue February 14, 2007
Received December 1, 2006

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Communication

Chiral Oxazaborolidine−Aluminum Bromide Complexes Are Unusually Powerful and Effective Catalysts for Enantioselective Diels−Alder Reactions

Abstract

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History

Recommend & Share

Related Content

Triflimide Activation of a Chiral Oxazaborolidine Leads to a More General Catalytic System for Enantioselective Diels−Alder Addition

Broad-Spectrum Enantioselective Diels−Alder Catalysis by Chiral, Cationic Oxazaborolidines

Enantioselective and Structure-Selective Diels−Alder Reactions of Unsymmetrical Quinones Catalyzed by a Chiral Oxazaborolidinium Cation. Predictive Selection Rules

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