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Issue 18, 2012
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CN-assisted oxidative cyclization of cyano cinnamates and styrene derivatives: a facile entry to 3-substituted chiral phthalides

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Abstract

The asymmetric dihydroxylation (AD) of o-cyano cinnamates and styrene derivatives leads to efficient construction of chiral phthalide frameworks in high optical purities. This unique reaction is characterized by unusual synergism between CN and osmate groups resulting in rate enhancement of the AD process. The method is amply demonstrated by the synthesis and the structural/stereochemical assignment of the natural products.

Graphical abstract: CN-assisted oxidative cyclization of cyano cinnamates and styrene derivatives: a facile entry to 3-substituted chiral phthalides

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Publication details

The article was received on 24 Feb 2012, accepted on 07 Mar 2012 and first published on 09 Mar 2012


Article type: Paper
DOI: 10.1039/C2OB25409C
Citation: Org. Biomol. Chem., 2012,10, 3655-3661
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    CN-assisted oxidative cyclization of cyano cinnamates and styrene derivatives: a facile entry to 3-substituted chiral phthalides

    R. S. Reddy, I. N. C. Kiran and A. Sudalai, Org. Biomol. Chem., 2012, 10, 3655
    DOI: 10.1039/C2OB25409C

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