N -Alkoxyacrylamides as Substrates for Enantioselective Diels−Alder Reactions
2002; American Chemical Society; Volume: 4; Issue: 10 Linguagem: Inglês
10.1021/ol0257981
ISSN1523-7060
AutoresOlivier Corminboeuf, Philippe Renaud,
Tópico(s)Advanced Synthetic Organic Chemistry
Resumo[reaction: see text] The use of N-alkoxyacrylamides as substrates for Lewis acid catalyzed Diels-Alder reactions has been examined. Enantioselectivities up to 92% ee have been achieved using very simple chiral Lewis acids prepared from triisobutylaluminum and 2,2-dimethyl-alpha,alpha,alpha',alpha'-tetra-1-naphthalenyl-TADDOL (1-NaphtTADDOL). The use of Yamamoto's Zn-BINOL, easily prepared from Et2Zn and 1,1'-bi-2-naphthol (BINOL), proved to be even more efficient, and enantioselectivities up to 96% ee were achieved.
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