Issue 9, 2016

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
08 Marts 2016
Accepted
19 Maijs 2016
First published
24 Maijs 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2016,7, 5934-5938

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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