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Synlett 2003(8): 1213-1220
DOI: 10.1055/s-2003-39903
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© Georg Thieme Verlag Stuttgart ˙ New York

Beyond Breaking the Mirror Plane: The Desymmetrisation of Centro­symmetric Molecules as an Efficient Strategy for Asymmetric Synthesis

Mark Anstiss, Joanne M. Holland, Adam Nelson*, James R. Titchmarsh
Department of Chemistry, University of Leeds, Leeds LS2 9JT, UK
e-Mail: Adam.Nelson@chemistry.leeds.ac.uk;
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Publication History

Received 28 March 2003
Publication Date:
11 June 2003 (online)

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Abstract

Enantioselective desymmetrisation is one of the most effective strategies for asymmetric synthesis. Typically, a meso starting material with an internal mirror plane is desymmetrised by reaction with a chiral reagent; excellent yields of products as single enantiomers may be obtained. In fact, this approach is amenable to the synthesis of compounds with any embedded improper element of symmetry (such as a centre of symmetry). This review concentrates on the strategies, which are available for the synthesis of centrosymmetric (and S 4-symmetric) molecules and describes methods for their desymmetrisation. Examples of syntheses of biologically active molecules and natural products are used.

Key words

asymmetric synthesis - desymmetrisation - internal mirror plane - natural product synthesis

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