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Issue 9, 2016
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Rhodium catalyzed diastereoselective synthesis of 2,2,3,3-tetrasubstituted indolines from N-sulfonyl-1,2,3-triazoles and ortho-vinylanilines

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Abstract

An efficient diastereoselective rhodium catalyzed synthesis of indolines possessing two contiguous tetrasubstituted carbon centers has been achieved with good to excellent yields using ortho-vinylanilines and iminocarbenes derived from N-sulfonyl-1,2,3-triazoles. The reaction affords excellent cis-diastereoselectivity through the initial formation of a N-ylide followed by intramolecular trapping with unactivated alkenes via an ene-type reaction with a well-organized transition state, namely intramolecular carbenylative amination of alkenes. The developed transformation was further extended to the successful synthesis of tricyclic compounds, imidazoindolines, through reduction and hypervalent iodine mediated oxidative cyclization.

Graphical abstract: Rhodium catalyzed diastereoselective synthesis of 2,2,3,3-tetrasubstituted indolines from N-sulfonyl-1,2,3-triazoles and ortho-vinylanilines

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Article information


Submitted
08 Mar 2016
Accepted
19 May 2016
First published
24 May 2016

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2016,7, 5934-5938
Article type
Edge Article

Rhodium catalyzed diastereoselective synthesis of 2,2,3,3-tetrasubstituted indolines from N-sulfonyl-1,2,3-triazoles and ortho-vinylanilines

D. Yadagiri, A. C. S. Reddy and P. Anbarasan, Chem. Sci., 2016, 7, 5934
DOI: 10.1039/C6SC01075J

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