Organic letters | 2019

Ni-Catalyzed β-Alkylation of Cyclopropanol-Derived Homoenolates.

 
 
 
 

Abstract


Metal homoenolates are valuable synthetic intermediates which provide access to β-functionalized ketones. In this report, we disclose a Ni-catalyzed β-alkylation reaction of cyclopropanol-derived homoenolates using redox-active N-hydroxyphthalimide (NHPI) esters as the alkylating reagents. The reaction is compatible with 1°, 2°, and 3° NHPI esters. Mechanistic studies imply radical activation of the NHPI ester and 2e β-carbon elimination occurring on the cyclopropanol.

Volume None
Pages None
DOI 10.1021/acs.orglett.9b03435
Language English
Journal Organic letters

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