Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, P R China.
Org Lett. 2011 Mar 4;13(5):936-9. doi: 10.1021/ol1029832. Epub 2011 Feb 10.
Multifunctionalized tetrahydroindan derivatives with four stereocenters were constructed via two sequential Michael reactions between cyclic γ,δ-unsaturated-β-ketoester and nitroalkenes initiated with 0.5-2 mol % of cinchona alkaloid based bifunctional organocatalysts and then with 1 equiv of tetramethylguanidine for cyclization. The desired products could be obtained in high yields (up to 99% yield) with excellent enantioselectivities (95-99% ee) as well as diastereoselectivities (up to >99:1 dr) even on a gram scale.
通过使用 0.5-2 mol% 的基于金鸡纳生物碱的双功能有机催化剂引发的环γ,δ-不饱和-β-酮酯与硝基亚烯烃之间的两个连续迈克尔反应，构建了具有四个立体中心的多功能四氢茚衍生物，然后用 1 当量的四甲基胍进行环化。即使在克级规模下，也可以以高收率（高达 99%的产率）和优异的对映选择性（95-99%ee）以及非对映选择性（高达>99:1 dr）获得所需产物。
