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Issue 8, 2008
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The conformational rigidity of butane-1,2-diacetals as a powerful synthetic tool

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Abstract

Butane-1,2-diacetals are selective protecting groups for trans-diequatorial-1,2-diols and have been widely used in carbohydrate chemistry. The scope of diacetal protection has been extended more recently to include other important hydroxylated chiral templates containing trans-1,2-diols, such as quinic and shikimic acids, the protection of which as diacetals leads to a strong conformational rigidity that induces excellent diastereoselectivity control. In addition, the chiral information stored in the diacetal backbone has also been exploited in the synthesis of important building blocks, such as glycerate, glycolate and tartrate diacetal derivatives. In this critical review, the synthetic power of the conformational rigidity and the chirality stored in the diacetal backbone is described. This phenomenon will be illustrated with recent examples of applications in the synthesis of natural products or biologically interesting compounds (80 references).

Graphical abstract: The conformational rigidity of butane-1,2-diacetals as a powerful synthetic tool

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Publication details

The article was received on 20 Mar 2008 and first published on 17 Jun 2008


Article type: Critical Review
DOI: 10.1039/B717902B
Chem. Soc. Rev., 2008,37, 1689-1708

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    The conformational rigidity of butane-1,2-diacetals as a powerful synthetic tool

    E. Lence, L. Castedo and C. González-Bello, Chem. Soc. Rev., 2008, 37, 1689
    DOI: 10.1039/B717902B

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