Rhodium catalyzed diastereoselective synthesis of 2,2,3,3-tetrasubstituted indolines from N-sulfonyl-1,2,3-triazoles and ortho-vinylanilines
Open Access
- 24 May 2016
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Science
- Vol. 7 (9), 5934-5938
- https://doi.org/10.1039/c6sc01075j
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.Funding Information
- Department of Science and Technology, Ministry of Science and Technology (SR/S1/OC-48/2012)
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