Department of Chemistry, Brooklyn College and the City University of New York, 2900 Bedford Avenue, Brooklyn, New York 11210, USA.
Org Lett. 2009 Dec 17;11(24):5654-7. doi: 10.1021/ol9024293.
While beta-ketoesters are useful Michael donors, they were previously ineffective in Michael-Michael cascade reactions using alpha,beta-unsaturated aldehydes in conjunction with diphenylprolinol silyl ether organocatalysts. However, through rational modification of substrates and manipulation of the catalytic cycle, we developed an efficient Michael-Michael cascade reaction using beta-ketoesters of type 9. In this transformation, highly substituted fused carbocycles are generated in a single step in up to 87% yield and 99% ee.
虽然β-酮酯是有用的迈克尔供体,但在使用α,β-不饱和醛与二苯脯醇硅醚有机催化剂的迈克尔-迈克尔级联反应中,它们之前是无效的。然而,通过对底物进行合理修饰和对催化循环进行操作,我们开发了一种使用 9 型β-酮酯的高效迈克尔-迈克尔级联反应。在这种转化中,高度取代的稠合碳环可以在一步中以高达 87%的收率和 99%的对映选择性生成。