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Issue 11, 2012
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Complex fragment coupling by crotylation: a powerful tool for polyketide natural product synthesis

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Abstract

The first examples of the use of crotylation as a stereocontrolled complex fragment coupling strategy are described. Asymmetric aldehyde isoprenylation provides access to 2-substituted-1,3-butadienes that may be subjected to highly regio- and stereoselective 1,4 hydrosilylation with trichloro-silane. After complexation with a chiral diamine, the 2-substituted-cis-crotylsilanes may be employed in highly diastereoselective Sc(OTf)3-catalyzed aldehdye crotylation reactions.

Graphical abstract: Complex fragment coupling by crotylation: a powerful tool for polyketide natural product synthesis

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Publication details

The article was received on 22 Aug 2012, accepted on 23 Aug 2012 and first published on 31 Aug 2012


Article type: Edge Article
DOI: 10.1039/C2SC21325G
Citation: Chem. Sci., 2012,3, 3326-3330
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    Complex fragment coupling by crotylation: a powerful tool for polyketide natural product synthesis

    S. K. Reznik, B. S. Marcus and J. L. Leighton, Chem. Sci., 2012, 3, 3326
    DOI: 10.1039/C2SC21325G

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