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Issue 7, 2013
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Enantioselective synthesis of hindered cyclic dialkyl ethers via catalytic oxa-Michael/Michael desymmetrization

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Abstract

An asymmetric oxa-Michael/Michael cascade reaction of p-quinols and α,β-unsaturated aldehydes provides access to hindered dialkyl ethers. A highly enantioselective oxa-Michael addition of a tertiary alcohol precedes an intramolecular cyclohexadienone desymmetrization, which allows for the concomitant formation of four contiguous stereocenters in a single step. The highly functionalized bicyclic frameworks are rapidly obtained from simple starting materials with good diastereoselection and serve as valuable precursors for further manipulation.

Graphical abstract: Enantioselective synthesis of hindered cyclic dialkyl ethers via catalytic oxa-Michael/Michael desymmetrization

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Publication details

The article was received on 17 Apr 2013, accepted on 14 May 2013 and first published on 24 May 2013


Article type: Edge Article
DOI: 10.1039/C3SC51022K
Citation: Chem. Sci., 2013,4, 2828-2832
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    Enantioselective synthesis of hindered cyclic dialkyl ethers via catalytic oxa-Michael/Michael desymmetrization

    M. T. Corbett and J. S. Johnson, Chem. Sci., 2013, 4, 2828
    DOI: 10.1039/C3SC51022K

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