Diastereo- and Enantioselective Formal [3 + 2] Cycloaddition of Cyclopropyl Ketones and Alkenes via Ti-Catalyzed Radical Redox Relay

• DOI: 10.1021/jacs.7b13710
• Publication Date: 2018-02-21T18:21:04Z
• Authors: Wei Hao; Johannes H. Haren...; Xiangyu Wu; Samantha N. MacMi...; Song Lin
• Keywords: Titanium; Cycloaddition Reaction; Free Radicals; Molecular Structure; Stereoisomerism; Cyclopentanes; Alkenes; Ketones; 01 natural sciences; Catalysis; 0104 chemical sciences; Oxidation-Reduction

We report a stereoselective formal [3 + 2] cycloaddition of cyclopropyl ketones and radical-acceptor alkenes to form polysubstituted cyclopentane derivatives. Catalyzed by a chiral Ti(salen) complex, the cycloaddition occurs via a radical redox-relay mechanism and constructs two C-C bonds and two contiguous stereogenic centers with generally excellent diastereo- and enantioselectivity.