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Highly Diastereoselective Synthesis of Trifluoromethyl Indolines by Interceptive Benzylic Decarboxylative Cycloaddition of Nonvinyl, Trifluoromethyl Benzoxazinanones with Sulfur Ylides under Palladium Catalysis

Nagender Punna, Pulakesh Das, Véronique Gouverneur and Norio Shibata*

*Department of Nanopharmaceutical Sciences & Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan, Email: nozshibanitech.ac.jp

N. Punna, P. Das, V. Gouverneur, N. Shibata, Org. Lett., 2018, 20, 1526-1529.

DOI: 10.1021/acs.orglett.8b00237 (free Supporting Information)


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Abstract

A Pd-catalyzed interceptive decarboxylative benzylic cycloaddition (IDBC) of nonvinyl, trifluoromethyl benzoxazinanones with sulfur ylides enables a highly diastereoselective synthesis of trifluoromethyl-substituted indolines via palladium-π-benzyl zwitterionic intermediates.

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Key Words

Indolines


ID: J54-Y2018