通过有机催化的双迈克尔加成反应对多取代环戊酮的对映选择性合成。
Enantioselective synthesis of polysubstituted cyclopentanones by organocatalytic double Michael addition reactions.
机构信息
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
出版信息
Org Lett. 2010 Aug 20;12(16):3634-7. doi: 10.1021/ol101414b.
PMID:20704408
Abstract
The O-TMS-protected diphenylprolinol-catalyzed cascade double Michael addition reactions of alpha,beta-unsaturated aldehydes with a beta-keto ester bearing a highly electron-deficient olefin unit occur smoothly to afford polysubstituted cyclopentanones. This process allows formation of four contiguous stereocenters in the cyclopentanone ring in one-step with excellent enantioselectivity.
摘要
O-TMS 保护的二苯基脯氨醇催化的α,β-不饱和醛与带有缺电子烯烃单元的β-酮酯的级联双迈克尔加成反应顺利进行，得到多取代的环戊酮。该过程允许在一步中以优异的对映选择性形成环戊酮环中的四个连续的立体中心。
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