Phosphine-phosphite ligands: Chelate ring size vs. activity and enantioselectivity relationships in asymmetric hydrogenation

Gergely Farkas, Szabolcs Balogh, József Madarász, Áron Szöllsy, Ferenc Darvas, László Ürge, Maryse Gouygou, J. Bakos

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Abstract

A series of new phosphine-phosphite ligands P(C) nOP (n = 1-4) have been synthesized and used for rhodium-catalyzed asymmetric hydrogenation of prochiral olefins in order to study the effect of the chelate ring size. Excellent ees (up to 97.5%) were obtained in the hydrogenation of dimethyl itaconate and an increase of activity and enantioselectivity was observed in the hydrogenation of (Z)-α-acetamidocinnamic acid methyl ester with the increasing length of the backbone of the ligands.

Original languageEnglish
Pages (from-to)9493-9502
Number of pages10
JournalDalton Transactions
Volume41
Issue number31
DOIs
Publication statusPublished - Aug 21 2012

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phosphine
Phosphites
Enantioselectivity
Hydrogenation
Ligands
Rhodium
Alkenes
Esters
Thermodynamic properties
Acids

ASJC Scopus subject areas

  • Inorganic Chemistry

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Phosphine-phosphite ligands : Chelate ring size vs. activity and enantioselectivity relationships in asymmetric hydrogenation. / Farkas, Gergely; Balogh, Szabolcs; Madarász, József; Szöllsy, Áron; Darvas, Ferenc; Ürge, László; Gouygou, Maryse; Bakos, J.

In: Dalton Transactions, Vol. 41, No. 31, 21.08.2012, p. 9493-9502.

Research output: Contribution to journalArticle

Farkas, G, Balogh, S, Madarász, J, Szöllsy, Á, Darvas, F, Ürge, L, Gouygou, M & Bakos, J 2012, 'Phosphine-phosphite ligands: Chelate ring size vs. activity and enantioselectivity relationships in asymmetric hydrogenation', Dalton Transactions, vol. 41, no. 31, pp. 9493-9502. https://doi.org/10.1039/c2dt30386h
Farkas, Gergely ; Balogh, Szabolcs ; Madarász, József ; Szöllsy, Áron ; Darvas, Ferenc ; Ürge, László ; Gouygou, Maryse ; Bakos, J. / Phosphine-phosphite ligands : Chelate ring size vs. activity and enantioselectivity relationships in asymmetric hydrogenation. In: Dalton Transactions. 2012 ; Vol. 41, No. 31. pp. 9493-9502.
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