Asymmetric Organocatalysis of 4 + 3 Cycloaddition Reactions
- 30 January 2003
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (8), 2058-2059
- https://doi.org/10.1021/ja029058z
Abstract
Treatment of several 4-trialkylsilyloxypentadienals with a chiral secondary amine, trifluoroacetic acid, and a diene resulted in the formation of 4 + 3 cycloaddition products, which were enantiomerically enriched. This represents the first examples of the asymmetric organocatalysis of the 4 + 3 cycloaddition reaction. 2,5-Dimethylfuran reacted with 4-trimethylsilyloxy-2,4-pentadienal in the presence of catalytic amounts of chiral amine and acid to afford a cycloadduct in 64% yield as a single diastereomer with an enantiomeric excess of 89%.This publication has 7 references indexed in Scilit:
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