Synthesis of substituted mandelic acid derivatives via enantioselective hydrogenation: Homogeneous versus heterogeneous catalysis

Advanced Synthesis and Catalysis

Volumn 346, Issue 7, 2004, Pages 842-848

  Cederbaum, Fredrik ^a   Lamberth, Clemens ^a   Malan, Christophe ^b   Naud, Fred ^b   Spindler, Felix ^b   Studer, Martin ^b   Blaser, Hans Ulrich ^b  

^a SYNGENTA CROP PROTECTION AG   (Switzerland)

^b SOLVIAS AG   (Switzerland)

Author keywords

keto esters; Cinchona alkaloids; Enantioselective hydrogenation; Mandelamide derivatives; MeObiphep; Platinum; Ruthenium

Indexed keywords

AMIDE; LIGAND; MANDELIC ACID DERIVATIVE; METAL; METHYL 4 CHLOROMANDELATE; METHYL 4 CHLOROPHENYLGLYOXYLATE; METHYL GROUP; PHENYLGLYOXYLIC ACID; PHOSPHINE DERIVATIVE; RHODIUM DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; CINCHONA; CRYSTALLIZATION; ENANTIOMER; ENANTIOSELECTIVITY; HYDROGENATION; SYNTHESIS;

EID: 4143105564     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404022     Document Type: Article

References (20)

1. R. G. Griffiths, J. Dancer, E. O'Neill, J. L. Harwood, New Phytologist 2003, 158, 345.
2. O. Ort, U. Döller, W. Reissel, S. D. Lindell, T. L. Hough, D. J. Simpson, J. P. Chung, Pesticide Sci. 1997, 50, 331.
3. R. Frey, S. G. Galbraith, S. Guelfi, C. Lamberth, M. Zeller, Synlett 2003, 1536.
4. a) For an overview, see: T. Ohkuma, R. Noyori, in: Comprehensive Asymmetric Catalysis, Vol. I, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, p. 199;
5. b) T. Chiba, A. Miyashita, H. Nohira, H. Takaya, Tetrahedron Lett. 1993, 34, 2351;
6. c) C. Pasquier, S. Naili, A. Mortreux, F. Agbossou, L. Pélinski, J. Brocard, J. Eilers, I. Reiners, V. Peper, J. Martens. Organometallics 2000, 19, 5723;
7. d) J. F. Carpentier, A. Mortreux, Tetrahedron: Asymmetry 1997, 8, 1083;
8. e) K. Mashima, K. Kusano, N. Sato, Y. Matsumura, K. Nozaki, H. Kumobayashi, N. Sayo, Y. Hori, T. Ishizaki, S. Akutagawa, H. Takaya, J. Org. Chem. 1994, 59, 3064.
9. a) For a recent overview, see: H.-U. Blaser, Ch. Malan, B. Pugin, F. Spindler, H. Steiner, M. Studer, Adv. Synth. Catal. 2003, 345, 103;
10. b) P. Gamez, F. Fache, M. Lemaire, Tetrahedron: Asymmetry 1995, #6#3, 705.
11. a) For a recent overview, see: M. Studer, H.-U. Blaser, Adv. Synth. Catal. 2003, 345, 45;
12. b) G. Z. Wang, T. Mallat, A. Baiker, Tetrahedron: Asymmetry 1997, 8, 2133;
13. c) M. Sutyinski, K. Szöri, K. Felföldi, M. Bartók, Catal. Commun. 2002, 2, 125;
14. d) C. Exner, A. Pfaltz, M. Studer, H.-U. Blaser, Adv. Synth. Catal. 2003, 345, 1253;
15. e) H.-U. Blaser, H. P. Jalett, F. Spindler, J. Mol. Catal. A: Chemical 1996, 107, 85.
16. F. Spindler, H. U. Blaser, Enantiomer 1999, 4, 557.
17. O. Itoh, T. Nagata, I. Nomura, T. Takanaga, T. Sugita, K. Ichikawa, Bull. Chem. Soc. Jpn. 1984, 57, 810.
18. I. T. Barnish, P. E. Cross, J. C. Danilewicz, R. P. Dickinson, D. A. Stopher, J. Med. Chem. 1981, 24, 399.
19. F. Cederbaum, A. De Mesmaeker, A. Jeanguenat, H.-J. Kempf, C. Lamberth, A. Schnyder, M. Zeller, R. Zeun, Chimia 2003, 57, 680.
20. K-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori, Angew. Chem. Int. Ed. Engl. 1997, 36, 285.