期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 14, 期 26, 页码 7867-7879出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200800442
关键词
unsaturated aldehydes; asymmetric catalysis; cyclopentanes; cyclopropanes; domino reactions; organocatalysis
资金
- Swedish National Research Council
- Wenner-Gren, Lars Hierta, Magnus Bergvall and Carl-Trygger Foundations
- VR
- Swedish Governmental Agency for Innovation Systems (VINNOVA)
The development of one-pot organocatalytic domino Michael/alpha-alkylation reactions between bromomalonates or bromoacetoacetate esters and alpha,beta-unsaturated aldehydes is presented. The chiral-amine-catalyzed reactions with bromomalonates as substrates give access to the corresponding 2-formylcyclopropane derivatives in high yields with excellent diastereoselectivity and up to 99% ee. The catalytic domino Michael/alpha-alkylation reactions between 4-bromo-acetoacetate and enals provide a route for the synthesis of functionalized cyclopentanones in good to high yields with 93-99% ee. The products from the organo-catalytic reactions were also reduced with high diastereoselectivity to the corresponding cyclopropanols and cyclopentanols, respectively. Moreover, one-pot combinations of amine and heterocyclic carbene catalysis (AHCC) enabled the highly enantioselective synthesis of P-malonate esters (91-97% ee) from the reaction between bromomalonates and enals. The tandem catalysis included the catalytic domino reaction followed by catalytic in situ chemoselective ring-opening of the 2-formylcyclopropane intermediates.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据