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

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.

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

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