Organic Chemistry Portal

Abstracts

Search:

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

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

*Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, Email: coreychemistry.harvard.edu

D. Liu, E. Canales, E. J. Corey, J. Am. Chem. Soc., 2007, 129, 1498-1499.

DOI: 10.1021/ja068637r (free Supporting Information)



see article for more reactions

Abstract

A 1:1 complex of AlBr3 with a chiral oxazaborolidine is a very potent Lewis acid catalyst for enantioselective Diels-Alder reactions. Only 4 mol % of the catalyst is required to achieve very high yields and enantiomeric purities over a broad range of achiral dienes and dienophiles.

see article for more examples



Key Words

Diels-Alder Reaction


ID: J48-Y2007-0410