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; Norio Shibata

doi:10.1021/acs.orglett.8b00237

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

Org Lett. 2018 Mar 16;20(6):1526-1529. doi: 10.1021/acs.orglett.8b00237. Epub 2018 Feb 23.

Authors

Nagender Punna¹, Pulakesh Das¹, Véronique Gouverneur², Norio Shibata^{1

3}

Affiliations

¹ Department of Nanopharmaceutical Sciences & Department of Life Science and Applied Chemistry , Nagoya Institute of Technology , Gokiso, Showa-ku, Nagoya 466-8555 , Japan.
² Chemistry Research Laboratory , University of Oxford , 12 Mansfield Road , Oxford OX1 3TA , U.K.
³ Institute of Advanced Fluorine-Containing Materials , Zhejiang Normal University , 688 Yingbin Avenue , 321004 Jinhua , China.

PMID: 29474077
DOI: 10.1021/acs.orglett.8b00237

Abstract

A highly diastereoselective synthesis of trifluoromethyl-substituted indolines under palladium catalysis is disclosed. The reaction proceeds by interceptive decarboxylative benzylic cycloaddition (IDBC) of nonvinyl, trifluoromethyl benzoxazinanones with sulfur ylides. The palladium-π-benzyl zwitterionic intermediates are suggested for this transformation, and this would be the first example of an IDBC reaction.

Publication types

Research Support, Non-U.S. Gov't