Enantioselective Diels−Alder Reactions with N -Hydroxy- N -phenylacrylamide
2002; American Chemical Society; Volume: 4; Issue: 10 Linguagem: Inglês
10.1021/ol025799t
ISSN1523-7060
AutoresOlivier Corminboeuf, Philippe Renaud,
Tópico(s)Molecular spectroscopy and chirality
Resumo[reaction: see text] The use of hydroxamic acids as templates for Lewis acid catalyzed enantioselective Diels-Alder reactions has been examined. A very simple chiral Lewis acid, prepared by mixing optically pure binaphthol with 3 equiv of trimethylaluminum, catalyzes the [4 + 2] cycloaddition of N-hydroxy-N-phenylacrylamide with cyclopentadiene at 0 degrees C in high yield (>96%) and with a fairly good level of enantioselectivity (91% ee). Facile conversion of the products to the corresponding alcohols or aldehydes makes the hydroxamic acid intermediates particularly useful.
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