This website uses cookies to give you the best user experience. If you continue
without changing your settings we'll assume you are happy to receive all RSC cookies.
You can change your cookie settings by navigating to our Privacy and Cookies page and following the instructions. These instructions
are also obtainable from the privacy link at the bottom of any RSC page.
Enantio- and diastereocontrolled conversion of chiral epoxides to trans-cyclopropane carboxylates: application to the synthesis of cascarillic acid, grenadamide and L-(−)-CCG-II
Division of Organic Chemistry, National Chemical Laboratory, Pune 411008, India
E-mail: pk.tripathi@ncl.res.in
; Fax: +91-20-25902629
; Tel: +91-20-25902050
Org. Biomol. Chem., 2012,10, 6987-6994
DOI:
10.1039/C2OB25622C
Received
26 Mar 2012,
Accepted
03 Jul 2012
First published online
04 Jul 2012
An efficient high yielding improved method for the enantio- and diastereoselective cyclopropanation of chiral epoxides using triethylphosphonoacetate and base (Wadsworth–Emmons cyclopropanation) is reported. The utility of this protocol is illustrated by concise and practical synthesis of cascarillic acid, grenadamide and L-(−)-CCG-II, a cyclopropane containing natural products.