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Nickel-Catalyzed Ring-Opening Allylation of Cyclopropanols via Homoenolate

Yoshiya Sekiguchi, Yan Ying Lee and Naohiko Yoshikai*

*Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan, Email: naohiko.yoshikai.c5tohoku.ac.jp

Y. Sekiguchi, Y. Y. Lee, N. Yoshikai, Org. Lett., 2021, 23, 5993-5997.

DOI: 10.1021/acs.orglett.1c02072 (free Supporting Information)


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Abstract

A nickel-catalyzed ring-opening allylation of cyclopropanols with allylic carbonates provides  δ,ε-unsaturated ketones in moderate to good yields under mild and neutral conditions. The reaction displays linear selectivity for both linear and branched acyclic allylic carbonates and is also applicable to cyclic allylic carbonates.


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proposed mechanism



Key Words

allylation, carbonyl compounds


ID: J54-Y2021