Issue 9, 2015
From the journal:

Organic Chemistry Frontiers

Kinetic resolution of racemic 5-alkylcyclohexenones via Pd(ii)-catalyzed 1,4-additions of arylboronic acids – access to trans 3-alkyl-5-arylcyclohexanones†

Kennard Gan,a   Abdul Sadeer,a   Jia Sheng Ng,a   Yunpeng Lu*a  and  Sumod A. Pullarkat*a  

* Corresponding authors

a Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, 21 Nanyang Link, Nanyang Technological University, Singapore 637371
E-mail: YPLu@ntu.edu.sg, sumod@ntu.edu.sg
Fax: (+) 6316-8906

Abstract

The kinetic resolution of racemic 5-substituted alkylcyclohexenones via 1, 4-conjugate addition with a variety of arylboronic acids was achieved by utilizing a ferrocenyl phosphapalladacycle catalyst. The addition reaction proceeded smoothly to afford trans-3-alkyl-5-arylcyclohexanones in good yields and selectivities.

Graphical abstract: Kinetic resolution of racemic 5-alkylcyclohexenones via Pd(ii)-catalyzed 1,4-additions of arylboronic acids – access to trans 3-alkyl-5-arylcyclohexanones

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Article information

DOI
https://doi.org/10.1039/C5QO00169B
Article type
Research Article
Submitted
27 May 2015
Accepted
02 Jul 2015
First published
03 Jul 2015

Org. Chem. Front., 2015,2, 1059-1065

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Kinetic resolution of racemic 5-alkylcyclohexenones via Pd(II)-catalyzed 1,4-additions of arylboronic acids – access to trans 3-alkyl-5-arylcyclohexanones

K. Gan, A. Sadeer, J. S. Ng, Y. Lu and S. A. Pullarkat, Org. Chem. Front., 2015, 2, 1059 DOI: 10.1039/C5QO00169B

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