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Synlett 2012; 23(20): 2903-2908
DOI: 10.1055/s-0032-1317556
DOI: 10.1055/s-0032-1317556
letter
Synthesis of Oxindole-Appended Allyl Amines and Vinyl Aziridines via InCl3/ArSH-Mediated Ring Opening of Vinyl Aziridines and Sulfur Ylide Aziridination
Further Information
Publication History
Received: 08 October 2012
Accepted after revision: 19 October 2012
Publication Date:
16 November 2012 (online)
Abstract
A short and efficient synthesis of oxindole-appended allyl amines and 3-vinylaziridine-2-oxindoles have been accomplished in good yield via InCl3/ArSH-mediated ring opening of 3-vinylaziridine-2-oxindoles and sulfur ylide aziridination, respectively. The sulfur ylide was generated in situ from the bromo isomerized Morita–Baylis–Hillman adduct of isatin with N-tosyl imines and tetrahydrothiophene under basic conditions.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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