Issue 18, 2012
From the journal:

Organic & Biomolecular Chemistry

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

R. Santhosh Reddy,a   I. N. Chaithanya Kirana  and  Arumugam Sudalai*a  

* Corresponding authors

a Chemical Engineering and Process Development Division National Chemical Laboratory, Pashan Road, Pune 411008, India
E-mail: a.sudalai@ncl.res.in
Fax: (+)91-02025902675

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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Article information

DOI
https://doi.org/10.1039/C2OB25409C
Article type
Paper
Submitted
24 Feb 2012
Accepted
07 Mar 2012
First published
09 Mar 2012

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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