Ru(arene)(amino alcohol)-Catalyzed Transfer Hydrogenation of Ketones:  Mechanism and Origin of Enantioselectivity

Author:

Alonso Diego A.1,Brandt Peter1,Nordin Sofia J. M.1,Andersson Pher G.1

Affiliation:

1. Contribution from the Department of Organic Chemistry, Uppsala University, Box 531, S-751 21 Uppsala, Sweden, and Department of Medicinal Chemistry, Royal Danish School of Pharmacy, Universitetsparken 2, DK-2100 Copenhagen, Denmark

Publisher

American Chemical Society (ACS)

Subject

Colloid and Surface Chemistry,Biochemistry,General Chemistry,Catalysis

Reference22 articles.

1. Asymmetric transfer hydrogenations:  (a) Gladiali, S.; Pinna, L.; Delogu, G.; De Martin, S.; Zassinovich, G.; Mestroni, G.Tetrahedron:  Asymmetry1990,1, 635. (b) Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A.Helv. Chim. Acta1991,74, 232. (c) Evans, D. A.; Nelson, S. G.; Gagné, M. R.; Muci, A. R.J.Am. Chem. Soc.1993,115, 9800. (d) Genet, J.P.; Ratovelomonana-Vidal, V.; Pinel, C.Synlett1993,34, 478. (e) Krasik, P.; Alper, H.Tetrahedron1994,50, 4347. (f) Yang, H.; Alvarez, M.; Lugan, N.; Mathieu, R.J. Chem. Soc.Chem. Commun.1995, 1721. (g) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R.J. Am. Chem. Soc.1995,117, 7562. (h) Gamez, P.; Fache, F.; Lemaire, M.Tetrahedron:  Asymmetry1995,6, 705. (i) Langer, T.; Helmchen, G.Tetrahedron Lett.1996,37, 1381. (j) Langer, T.; Janssen, J.; Helmchen, G.Tetrahedron:  Asymmetry1996,7, 1599. (k) Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X.Tetrahedron Lett.1996,37, 797. (l) Püntener, K.; Schwink, L.; Knochel, P.Tetrahedron Lett.1996,37, 8165. (m) Gamez, P.; Dunjic, B.; Lemaire, M.J. Org. Chem.1996,61, 5196. (n) Gao, J.X.; Ikariya, T.; Noyori, R.Organometallics1996,15, 1087. (o) Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X.Tetrahedron Lett.1997,38, 215. (p) Sammakia, T.; Stangeland, E. L.J. Org. Chem.1997,62, 6104. (q) Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R.J. Am. Chem. Soc.1997,119, 8738. (r) Palmer, M.; Walsgrove, T.; Wills, M.J. Org. Chem.1997,62, 5226. (s) Inoue, S.I.; Nomura, K.; Hashiguchi, S.; Noyori, R.; Izawa, Y.Chem. Lett.1997, 657. (t) Halle, R.; Schulz, E.; Lemaire, M.Synlett1997, 1257. (u) Touchard, F.; Fache, F.; Lemaire, M.Tetrahedron: Asymmetry1997,8, 3319. (v) Ohta, T.; Nakahara, S.; Shigemura, Y.; Hattori, K.; Furukawa, I.Chem. Lett.1998, 491. (w) Schwink, L.; Ireland, T.; Püntener, K.; Knochel, P.Tetrahedron:  Asymmetry1998,9, 1143. (x) Bayston, D. J.; Travers, C. B.; Polywka, M. E. C.Tetrahedron:  Asymmetry1998,9, 2015. (y) Jiang, Y.; Jiang, Q.; Zhang, X.J. Am. Chem. Soc.1998,120, 3817. (z) Everaere, K.; Carpentier, J.F.; Mortreux, A.; Bulliard, M.Tetrahedron:  Asymmetry1998,9, 2971. (aa) Breysse, E.; Pinel, C.; Lemaire, M.Tetrahedron:  Asymmetry1998,9, 897. (bb) Arikawa, Y.; Ueoka, M.; Matoba, K.; Nishibayashi, Y.; Haidai, M.; Uemura, S.J. Organomet. Chem.1999,572, 163.

2. Amino alcohol effects on the ruthenium(II)-catalysed asymmetric transfer hydrogenation of ketones in propan-2-ol

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