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Issue 21, 2012
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Diastereoselective 1,3-dipolar cycloaddition of pyrylium ylides with chiral enamides

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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

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Article information


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
Article type
Paper

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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