Department of Organic Chemistry, University of Geneva, quai Ernest Ansermet 30, CH-1211 Geneva 4, Switzerland.
Org Lett. 2013 May 3;15(9):2172-5. doi: 10.1021/ol400697n. Epub 2013 Apr 22.
The first organocatalytic diastereo- and enantioselective domino Michael/aldol reaction of 3-halogeno-1,2-diones to α,β-unsaturated aldehydes has been achieved. This transformation tolerates a large variety of electronically different substituents on both reactive partners and allows the synthesis of challenging cyclopentanone derivatives with four contiguous stereogenic centers in excellent diastereoselectivities (>20:1 dr) as well as good yields (69-97%), and enantioselectivities (up to 94% ee).
已实现 3-卤代-1,2-二酮与α,β-不饱和醛的首例有机催化非对映和对映选择性的串联迈克尔/羟醛缩合反应。这种转化可以容忍两种反应试剂上大量不同的电子取代基，并且允许以优异的非对映选择性（>20:1 dr）和良好的收率（69-97％）以及对映选择性（高达 94％ee）合成具有四个连续立体中心的具有挑战性的环戊酮衍生物。
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