Asymmetric Diels-Alder reactions of α,β-unsaturated aldehydes catalyzed by a diarylprolinol silyl ether salt in the presence of water

被引:134
作者
Hayashi, Yujiro [1 ]
Samanta, Sampak [1 ]
Gotoh, Hiroaki [1 ]
Ishikawa, Hayato [1 ]
机构
[1] Tokyo Univ Sci, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan
关键词
asymmetric synthesis; cycloaddition; enantioselectivity; organocatalysis; water chemistry;
D O I
10.1002/anie.200801408
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Water, water, everywhere: The title reaction predominantly affords the exo isomer with excellent enantioselectivity (see scheme; TMS=trimethylsilyl). The synthesis can be carried out without organic solvents and provides the products by distillation. Water increases the rate and enantioselectivity of the reaction. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6634 / 6637
页数:4
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