Organocatalytic dynamic kinetic resolution via conjugate addition: synthesis of chiral trans-2,5-dialkylcyclohexanones

Ganesh Pandey; Priyanka A. Adate; Vedavati G. Puranik

doi:10.1039/C2OB26597D

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Organic & Biomolecular Chemistry

Issue 41, 2012

The international home of synthetic, physical and biomolecular organic chemistry.

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Paper

Organocatalytic dynamic kinetic resolution via conjugate addition: synthesis of chiral trans-2,5-dialkylcyclohexanones

Ganesh Pandey,*^a Priyanka A. Adate^a and Vedavati G. Puranik^b

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Division of Organic Chemistry, National Chemical Laboratory, Pune-411 008, India
E-mail: gp.pandey@ncl.res.in ;
Fax: +91 20 2590-2628 ;
Tel: +91 20 2590-2281

Centre for Material Characterization, National Chemical Laboratory, Pune-411 008, India
E-mail: vg.puranikncl.res.in

Org. Biomol. Chem., 2012,10, 8260-8267

DOI: 10.1039/C2OB26597D
Received 09 Apr 2012, Accepted 24 Aug 2012
First published online 28 Aug 2012

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Abstract
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A novel strategy of initiating an organocatalysed dynamic kinetic resolution (dr up to 99:1 and er up to 94:6) for the synthesis of chiral trans-2,5-dialkylcyclohexanones by an asymmetric conjugate addition of dimethyl malonate on to 6-substituted cyclohexenones is reported.