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Issue 13, 2014
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Recent developments of direct rhenium-catalyzed [1,3]-transpositions of allylic alcohols and their silyl ethers

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Abstract

The direct metal-catalyzed [1,3]-transposition of allylic alcohols and allylic silyl ethers is a synthetically useful isomerization process that occurs via [3,3]-sigmatropic rearrangement induced by high oxidation state oxometal complexes. The isomerization requires only a catalytic amount of promoter, and high chirality transfer can be achieved. Thus, it bears a significant potential to become a powerful tool in multistep synthesis. Although [1,3]-transposition of allylic alcohols has been known since the late 1960s, the development of synthetically useful protocols that allow for a high level of regio- and stereoselectivity control and their synthetic applications have emerged only recently. This tutorial review summarizes recently developed regioselective [1,3]-transpositions of allylic alcohols and silyl ethers and their applications to natural product synthesis.

Graphical abstract: Recent developments of direct rhenium-catalyzed [1,3]-transpositions of allylic alcohols and their silyl ethers

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Publication details

The article was received on 20 Jan 2014 and first published on 24 Apr 2014


Article type: Tutorial Review
DOI: 10.1039/C4CS00036F
Citation: Chem. Soc. Rev., 2014,43, 4381-4394
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    Recent developments of direct rhenium-catalyzed [1,3]-transpositions of allylic alcohols and their silyl ethers

    I. Volchkov and D. Lee, Chem. Soc. Rev., 2014, 43, 4381
    DOI: 10.1039/C4CS00036F

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