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Phosphine-catalyzed [3 + 2] cycloadditions of trifluoromethyl enynes/enediynes with allenoates: access to cyclopentenes containing a CF3-substituted quaternary carbon center

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Abstract

Herein, the first use of trifluoromethyl-substituted enynes/enediynes as non-classical electron-deficient olefins for phosphine-catalyzed [3 + 2] cycloaddition with allenoates is reported. This reaction occurs with excellent regioselectivity under mild conditions, affording alkyne- and diyne-tethered cyclopentene derivatives containing a CF3-substituted quaternary carbon center in moderate to good yields.

Graphical abstract: Phosphine-catalyzed [3 + 2] cycloadditions of trifluoromethyl enynes/enediynes with allenoates: access to cyclopentenes containing a CF3-substituted quaternary carbon center

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Article information


Submitted
07 Jul 2020
Accepted
11 Sep 2020
First published
16 Sep 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Phosphine-catalyzed [3 + 2] cycloadditions of trifluoromethyl enynes/enediynes with allenoates: access to cyclopentenes containing a CF3-substituted quaternary carbon center

S. Chen, G. Chen, J. Zhang, Z. Li, Y. Zhao and Y. Liu, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00807A

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