Exploiting predisposition in the stereoselective synthesis of mono-, bi- and tetracyclic oxygen heterocycles: Equilibration between, and trapping of, alternative di- and tetraacetals

Stephen Bartlett; Robert Hodgson; Joanne M. Holland; Matthew Jones; Colin Kilner; Adam Nelson; Stuart Warriner

doi:10.1039/B303089J

Exploiting predisposition in the stereoselective synthesis of mono-, bi- and tetracyclic oxygen heterocycles: Equilibration between, and trapping of, alternative di- and tetraacetals

Stephen Bartlett,^a Robert Hodgson,^a Joanne M. Holland,^a Matthew Jones,^a Colin Kilner,^a Adam Nelson*^a and Stuart Warriner^a

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^a Department of Chemistry, University of Leeds, Leeds, UK

Abstract

The desymmetrisation of 1,4-difuran-2-ylbutane-1,4-diol by Sharpless asymmetric oxidation gave the corresponding desymmetrised product in > 96% ee. However, the product existed as a mixture of two interconverting isomers, both of which were mixtures of anomers. The product could be trapped in high yield with a range of reagents to give stable adducts with embedded pyran-3-one, 1,6-dioxaspiro[4.5]decane or pyrano[3,2-b]pyran ring systems. The strategy was also applied in the interconversion between alternative tetracycles and, under acidic conditions, this process was thermodynamically controlled. The selectivity of the process was rationalised by molecular modelling using the HF/6-31G* parameter set.

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Publication details

The article was received on 21 Mar 2003, accepted on 14 May 2003 and first published on 05 Jun 2003

Article type: Paper

DOI: 10.1039/B303089J

Citation: Org. Biomol. Chem., 2003,1, 2393-2402

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Exploiting predisposition in the stereoselective synthesis of mono-, bi- and tetracyclic oxygen heterocycles: Equilibration between, and trapping of, alternative di- and tetraacetals

S. Bartlett, R. Hodgson, J. M. Holland, M. Jones, C. Kilner, A. Nelson and S. Warriner, Org. Biomol. Chem., 2003, 1, 2393
DOI: 10.1039/B303089J
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Organic & Biomolecular Chemistry

Exploiting predisposition in the stereoselective synthesis of mono-, bi- and tetracyclic oxygen heterocycles: Equilibration between, and trapping of, alternative di- and tetraacetals

Abstract

Supplementary files

Publication details

Exploiting predisposition in the stereoselective synthesis of mono-, bi- and tetracyclic oxygen heterocycles: Equilibration between, and trapping of, alternative di- and tetraacetals

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