Events The 16th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 16th International Electronic Conference on Synthetic Organic Chemistry

Published date

30 Oct, 2012

Citation

Martial Toffano, Angelika Lásiková, Tibor Gracza, Giang Vo-Thanh, Jana Doháňošová, Kinetic resolution of Pent-4-ene-1,3-diol by Pd(II)-catalysed Oxycarbonylation in Ionic Liquids, in Proceedings of The 16th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2012, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-16-01089

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Kinetic resolution of Pent-4-ene-1,3-diol by Pd(II)-catalysed Oxycarbonylation in Ionic Liquids

Jana Doháňošová ¹

Giang Vo-Thanh ²

Tibor Gracza ¹

Angelika Lásiková ¹

Martial Toffano ²

1. Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovakia,

2. University Paris-Sud 11, ICMMO, Orsay Cedex France

Abstract

The first example of the use of ionic liquids as reaction media in the asymmetric Pd(II)-catalysed oxycarbonylation was investigated. Based on a ligand screening, the chiral box-type ligands were successfully used in the Pd(II)-promoted bicyclisation of pent-4-ene-1,3 diol (±)-1. The kinetic resolution of (±)-1 in the presence of chiral catalyst, p-benzoquinone and acetic acid in ionic liquids under carbon monoxide atmosphere afforded enantioenriched 2,6-dioxabicyclo[3.3.0]octane-3-ones (S,S)-2 (80% ee) and (R,R)-2 (57% ee), respectively.

Keywords

Kinetic resolution

oxycarbonylation

chiral ligand

asymmetric catalysis

ionic liquids.

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