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Issue 27, 2013
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Enantioselective Mukaiyama–Michael with 2-enoyl pyridine N-oxides catalyzed by PYBOX-DIPH-Zn(II)-complexes at ambient temperature

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Abstract

A chiral PYBOX-DIPH-Zn(II) catalyzed enantioselective Mukaiyama–Michael reaction of acyclic silyl enol ethers with 2-enoylpyridine N-oxides has been studied in external additive free conditions at ambient temperature. The methodology offers straightforward access to a variety of functionalized chiral 1,5-dicarbonyl compounds, which could easily be elaborated into synthetically viable pyrones via hydrolysis followed by cyclization. A transition state model has been proposed to explain the stereochemical outcome.

Graphical abstract: Enantioselective Mukaiyama–Michael with 2-enoyl pyridine N-oxides catalyzed by PYBOX-DIPH-Zn(ii)-complexes at ambient temperature

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Publication details

The article was received on 05 Mar 2013, accepted on 13 May 2013, published on 31 May 2013 and first published online on 31 May 2013


Article type: Paper
DOI: 10.1039/C3OB40445E
Citation: Org. Biomol. Chem., 2013,11, 4537-4545
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    Enantioselective Mukaiyama–Michael with 2-enoyl pyridine N-oxides catalyzed by PYBOX-DIPH-Zn(II)-complexes at ambient temperature

    S. Rout, S. K. Ray and V. K. Singh, Org. Biomol. Chem., 2013, 11, 4537
    DOI: 10.1039/C3OB40445E

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