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Issue 22, 2004
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Double diastereoselective SuperQuat glycolate aldol reactions: Application to the asymmetric synthesis of polyfunctionalised lactones

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Abstract

Polyfunctionalised lactones with up to five contiguous stereocentres may be prepared with high stereocontrol by a double diastereoselective aldol protocol with protected homochiral α,β-dihydroxy- or α,β-γ-trihydroxyaldehydes and a chiral glycolate oxazolidinone, followed by subsequent O-desilylation and lactonisation.

Graphical abstract: Double diastereoselective SuperQuat glycolate aldol reactions: Application to the asymmetric synthesis of polyfunctionalised lactones

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Publication details

The article was received on 30 Jul 2004, accepted on 13 Sep 2004 and first published on 11 Oct 2004


Article type: Paper
DOI: 10.1039/B411724G
Citation: Org. Biomol. Chem., 2004,2, 3385-3400
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    Double diastereoselective SuperQuat glycolate aldol reactions: Application to the asymmetric synthesis of polyfunctionalised lactones

    S. G. Davies, R. L. Nicholson and A. D. Smith, Org. Biomol. Chem., 2004, 2, 3385
    DOI: 10.1039/B411724G

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