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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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Publication details

The article was received on 29 Nov 2011, accepted on 19 Mar 2012 and first published on 19 Mar 2012


Article type: Paper
DOI: 10.1039/C2OB07007C
Citation: Org. Biomol. Chem., 2012,10, 4215-4219
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    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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