Hao W.
Harenberg JH.
Wu X.
MacMillan SN.
Lin S.
* Cornell University, Ithaca, USA and Ludwig-Maximilians-Universität München, Germany
Diastereo- and Enantioselective Formal [3+2] Cycloaddition of Cyclopropyl Ketones
and Alkenes via Ti-Catalyzed Radical Redox Relay.
J. Am. Chem. Soc. 2018;
140: 3514-3517
Key words
titanium catalysis - cycloaddition - cyclopropyl ketones - alkenes
Significance
The discovery of new reactions mediated by organic radical intermediates continues
to provide solutions to challenging synthetic problems in conventional two-electron
chemistry. The authors have developed a Ti-catalyzed stereoselective formal [3+2]
cycloaddition of cyclopropyl ketones and alkenes.
Comment
This catalytic cycloaddition through a radical-redox-relay mechanism provides chiral
polysubstituted cyclopentane derivatives containing two contiguous stereogenic centers
in high yields and with high diastereo- and enantioselectivities.
