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Synfacts 2007(3): 0323-0323  
DOI: 10.1055/s-2007-968239
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Organocatalytic Aryloxylation of Aldehydes with o-Quinones

Contributor(s): Benjamin List, Subhas Chandra Pan
F. A. Hernandez-Juan, D. M. Cockfield, D. J. Dixon*
University of Manchester, UK
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Publication History

Publication Date:
20 February 2007 (online)

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Significance

Here the authors report a direct enantioselective organocatalytic aryloxylation of aldehydes via an inverse-electron-demand hetero-Diels-Alder reaction of in situ generated en­amines and o-quinone reagents. MacMillan’s imidazolidinone catalyst 1 has been found to be effective for this reaction and MeCN-H2O has been identified as the optimal solvent system. With 10 mol% of the catalyst, moderate to good yields (52-75%) and high enantioselectivities (er = 88:12 to 90:10) are obtained for different alkyl aldehydes.