Enantioselective hydride transfer hydrogenation of ketones catalyzed by [(η6-p-cymene)Ru(amino acidato)Cl] and [(η6-p-cymene)Ru(amino acidato)]3(BF4)3 complexes

A. Kathó, Daniel Carmona, Fernando Viguri, Carlos D. Remacha, J. ózsef Kovács, Ferenc Joó, Luis A. Oro

Research output: Contribution to journalArticle

86 Citations (Scopus)

Abstract

The new complexes (RRuSC, SRuSC)-[(η6-pCym)Ru(L-Aze)Cl] (6a, b), (RRuSC, SRuSC)-[(η6-pCym)Ru(L-Pip)Cl] (7a, b), (RRuRRuRRuSCSCSCSNSNSN, SRuSRuSRuSCSCSCSNSNSN)-[{(η6-pCym)Ru(L-Aze)}3](BF4)3 (8a, b) and (RRuRRuRRuSCSCSCSNSNSN, SRuSRuSRuSCSCSCSNSNSN)-[{(η6-pCym)Ru(L-Pip)}3](BF4)3 (9a, b) (L-Aze=L-2-azetidinecarboxylate, L-Pip=L-2-piperidinecarboxylate) were prepared, characterized and used, together with the known [{(η6-pCym)Ru(L-Pro)}3](BF4)3, 5 and [{(η6-pCym)Ru(L-Ala)}3](BF4)3, 10 (L-Pro=L-prolinate, L-Ala=L-alaninate), in hydride transfer reduction of acetophenone, a series of substituted acetophenones and several other ketones with moderate to high conversions and enantioselectivities up to 86% e.e.

Original languageEnglish
Pages (from-to)299-306
Number of pages8
JournalJournal of Organometallic Chemistry
Volume593-594
Publication statusPublished - Jan 15 2000

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Acetophenones
Hydrogenation
Enantioselectivity
Ketones
Hydrides
ketones
hydrogenation
hydrides
acetophenone
4-cymene

Keywords

  • Amino acids
  • Asymmetric catalysis
  • Hydrogenation
  • Ketones
  • Ruthenium

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry

Cite this

Enantioselective hydride transfer hydrogenation of ketones catalyzed by [(η6-p-cymene)Ru(amino acidato)Cl] and [(η6-p-cymene)Ru(amino acidato)]3(BF4)3 complexes. / Kathó, A.; Carmona, Daniel; Viguri, Fernando; Remacha, Carlos D.; Kovács, J. ózsef; Joó, Ferenc; Oro, Luis A.

In: Journal of Organometallic Chemistry, Vol. 593-594, 15.01.2000, p. 299-306.

Research output: Contribution to journalArticle

Kathó, A. ; Carmona, Daniel ; Viguri, Fernando ; Remacha, Carlos D. ; Kovács, J. ózsef ; Joó, Ferenc ; Oro, Luis A. / Enantioselective hydride transfer hydrogenation of ketones catalyzed by [(η6-p-cymene)Ru(amino acidato)Cl] and [(η6-p-cymene)Ru(amino acidato)]3(BF4)3 complexes. In: Journal of Organometallic Chemistry. 2000 ; Vol. 593-594. pp. 299-306.
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abstract = "The new complexes (RRuSC, SRuSC)-[(η6-pCym)Ru(L-Aze)Cl] (6a, b), (RRuSC, SRuSC)-[(η6-pCym)Ru(L-Pip)Cl] (7a, b), (RRuRRuRRuSCSCSCSNSNSN, SRuSRuSRuSCSCSCSNSNSN)-[{(η6-pCym)Ru(L-Aze)}3](BF4)3 (8a, b) and (RRuRRuRRuSCSCSCSNSNSN, SRuSRuSRuSCSCSCSNSNSN)-[{(η6-pCym)Ru(L-Pip)}3](BF4)3 (9a, b) (L-Aze=L-2-azetidinecarboxylate, L-Pip=L-2-piperidinecarboxylate) were prepared, characterized and used, together with the known [{(η6-pCym)Ru(L-Pro)}3](BF4)3, 5 and [{(η6-pCym)Ru(L-Ala)}3](BF4)3, 10 (L-Pro=L-prolinate, L-Ala=L-alaninate), in hydride transfer reduction of acetophenone, a series of substituted acetophenones and several other ketones with moderate to high conversions and enantioselectivities up to 86{\%} e.e.",
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T1 - Enantioselective hydride transfer hydrogenation of ketones catalyzed by [(η6-p-cymene)Ru(amino acidato)Cl] and [(η6-p-cymene)Ru(amino acidato)]3(BF4)3 complexes

AU - Kathó, A.

AU - Carmona, Daniel

AU - Viguri, Fernando

AU - Remacha, Carlos D.

AU - Kovács, J. ózsef

AU - Joó, Ferenc

AU - Oro, Luis A.

PY - 2000/1/15

Y1 - 2000/1/15

N2 - The new complexes (RRuSC, SRuSC)-[(η6-pCym)Ru(L-Aze)Cl] (6a, b), (RRuSC, SRuSC)-[(η6-pCym)Ru(L-Pip)Cl] (7a, b), (RRuRRuRRuSCSCSCSNSNSN, SRuSRuSRuSCSCSCSNSNSN)-[{(η6-pCym)Ru(L-Aze)}3](BF4)3 (8a, b) and (RRuRRuRRuSCSCSCSNSNSN, SRuSRuSRuSCSCSCSNSNSN)-[{(η6-pCym)Ru(L-Pip)}3](BF4)3 (9a, b) (L-Aze=L-2-azetidinecarboxylate, L-Pip=L-2-piperidinecarboxylate) were prepared, characterized and used, together with the known [{(η6-pCym)Ru(L-Pro)}3](BF4)3, 5 and [{(η6-pCym)Ru(L-Ala)}3](BF4)3, 10 (L-Pro=L-prolinate, L-Ala=L-alaninate), in hydride transfer reduction of acetophenone, a series of substituted acetophenones and several other ketones with moderate to high conversions and enantioselectivities up to 86% e.e.

AB - The new complexes (RRuSC, SRuSC)-[(η6-pCym)Ru(L-Aze)Cl] (6a, b), (RRuSC, SRuSC)-[(η6-pCym)Ru(L-Pip)Cl] (7a, b), (RRuRRuRRuSCSCSCSNSNSN, SRuSRuSRuSCSCSCSNSNSN)-[{(η6-pCym)Ru(L-Aze)}3](BF4)3 (8a, b) and (RRuRRuRRuSCSCSCSNSNSN, SRuSRuSRuSCSCSCSNSNSN)-[{(η6-pCym)Ru(L-Pip)}3](BF4)3 (9a, b) (L-Aze=L-2-azetidinecarboxylate, L-Pip=L-2-piperidinecarboxylate) were prepared, characterized and used, together with the known [{(η6-pCym)Ru(L-Pro)}3](BF4)3, 5 and [{(η6-pCym)Ru(L-Ala)}3](BF4)3, 10 (L-Pro=L-prolinate, L-Ala=L-alaninate), in hydride transfer reduction of acetophenone, a series of substituted acetophenones and several other ketones with moderate to high conversions and enantioselectivities up to 86% e.e.

KW - Amino acids

KW - Asymmetric catalysis

KW - Hydrogenation

KW - Ketones

KW - Ruthenium

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M3 - Article

VL - 593-594

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EP - 306

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

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