Issue 21, 2012

Diastereoselective 1,3-dipolar cycloaddition of pyrylium ylides with chiral enamides

Abstract

Chiral enamides 5f–i were found to react with pyrylium ylides to give cycloadducts 6d–i in good yields with an excellent level of stereoselectivity. The chiral auxiliary was successfully removed on hydrogenolysis of compound 6f in continuous flow (H-Cube) resulting in the first asymmetric synthesis of complex amine 8.

Graphical abstract: Diastereoselective 1,3-dipolar cycloaddition of pyrylium ylides with chiral enamides

Supplementary files

Article information

Article type
Paper
Submitted
29 Nov 2011
Accepted
19 Mar 2012
First published
19 Mar 2012
This article is Open Access

Org. Biomol. Chem., 2012,10, 4215-4219

Diastereoselective 1,3-dipolar cycloaddition of pyrylium ylides with chiral enamides

K. Tchabanenko, C. Sloan, Y. Bunetel and P. Mullen, Org. Biomol. Chem., 2012, 10, 4215 DOI: 10.1039/C2OB07007C

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