%0 Journal Article %A Harmata, Michael %A Ghosh, Sunil K. %A Hong, Xuechuan %A Wacharasindhu, Sumrit %A Kirchhoefer, Patrick %D 2003 %T Asymmetric Organocatalysis of 4 + 3 Cycloaddition Reactions %U https://acs.figshare.com/articles/journal_contribution/Asymmetric_Organocatalysis_of_4_3_Cycloaddition_Reactions/3647337 %R 10.1021/ja029058z.s002 %2 https://ndownloader.figshare.com/files/5736198 %K presence %K Asymmetric Organocatalysis %K diene %K enantiomerically %K cycloadduct %K 3 Cycloaddition Reactions Treatment %K trifluoroacetic acid %K Dimethylfuran %K chiral amine %K diastereomer %K enantiomeric %K formation %K 3 cycloaddition reaction %K trialkylsilyloxypentadienal %K 3 cycloaddition products %K organocatalysi %K trimethylsilyloxy %X 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%. %I ACS Publications