Synfacts 2018; 14(05): 0483
DOI: 10.1055/s-0037-1609451
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Titanium-Catalyzed Stereoselective Formal [3+2] Cycloaddition

Hisashi Yamamoto
Wataru Muramatsu
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
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Publication History

Publication Date:
17 April 2018 (online)



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.



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.