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Synfacts 2018; 14(05): 0483
DOI: 10.1055/s-0037-1609451
DOI: 10.1055/s-0037-1609451
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Titanium-Catalyzed Stereoselective Formal [3+2] Cycloaddition
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
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
Further Information
Publication History
Publication Date:
17 April 2018 (online)
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.
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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.
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