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Critical solvent effect on the chiral recognition of a catalytic species by a chiral substrate

✍ Scribed by Lisa Diab; Maryse Gouygou; Eric Manoury; Philippe Kalck; Martine Urrutigoïty

Publisher: Elsevier Science
Year: 2007
Tongue: English
Weight: 201 KB
Volume: 278
Category: Article
ISSN: 1381-1169
DOI: 10.1016/j.molcata.2007.08.025

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✦ Synopsis

In the diastereoselective cyclocarbonylation of isopulegol and isolimonene catalysed by the non-chiral [PdCl 2 L 2 ] palladium complexes (L = PPh 3 , L 2 = bis(diphenylphosphino)-butane or -ferrocene), the diastereoisomeric excess is enhanced by a factor of 1.5-2 when toluene is substituted by chloro-solvents. A less significant effect is noted when using more coordinating solvents such as acetonitrile and THF. In chloro-solvents reaction rates are faster than in toluene, isopropanol, acetonitrile or THF.

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