Achiral ligands dramatically enhance rate and enantioselectivity in the Rh/phosphoramidite-catalyzed hydrogenation of α,β-disubstituted unsaturated acids

Angewandte Chemie - International Edition

Volumn 44, Issue 27, 2005, Pages 4209-4212

  Hoen, Rob ^a   Boogers, Jeroen A F ^b   Bernsmann, Heiko ^a   Minnaard, Adriaan J ^a   Meetsma, Auke ^a   Tiemersma Wegman, Theodora D ^a   De Vries, André H M ^b   De Vries, Johannes G ^b   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b DSM Pharmaceutical Products   (Netherlands)

Author keywords

Asymmetric catalysis; Hydrogenation; Ligand effects; Phosphines; Rhodium

Indexed keywords

CARBOXYLIC ACIDS; CATALYSIS; COMPLEXATION; HYDROGENATION; PHOSPHORUS COMPOUNDS; RHODIUM COMPOUNDS;

CHIRALS; CINNAMIC ACIDS; ENANTIOSELECTIVITY; LIGAND;

CATALYSTS;

ACID; ACRYLIC ACID; ACRYLIC ACID DERIVATIVE; ALPHA METHYLCINNAMIC ACID; ALPHA-METHYLCINNAMIC ACID; HYDROGEN; LIGAND; METHACRYLIC ACID DERIVATIVE; ORGANOPHOSPHORUS COMPOUND; PHENYLPROPIONIC ACID DERIVATIVE; PHOSPHORAMIDOUS ACID; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ACIDS; ACRYLATES; CATALYSIS; HYDROGEN; LIGANDS; METHACRYLATES; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; PHENYLPROPIONATES; RHODIUM; STEREOISOMERISM;

EID: 22144464492     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200500784     Document Type: Article

References (39)

1. a) C. Claver, E. Fernandez, A. Gillon, K. Heslop, D. J. Hyett, A. Martorell, A. G. Orpen, P. G. Pringle, Chem. Commun. 2000, 961;
2. b) M. T. Reetz, G. Mehler, Angew. Chem. 2000, 112, 4047;
3. Angew. Chem. Int. Ed. 2000, 39, 3889;
4. c) M. Van den Berg, A. J. Minnaard, E. P. Schudde, J. Van Esch, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, J. Am. Chem. Soc. 2000, 122, 11539.
5. a) M. T. Reetz, T. Sell, A. Meiswinkel, G. Mehler. Angew. Chem. 2003, 115, 814;
6. Angew. Chem. Int. Ed. 2003, 42, 790;
7. b) D. Peña, A. J. Minnaard, J. A. F. Boogers, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, Org. Biomol. Chem. 2003, 1, 1087.
8. a) M. T. Reetz, G. Mehler, Tetrahedron Lett. 2003, 44, 4593;
9. b) M. T. Reetz, Chim. Oggi 2003, 21, 5;
10. c) M. T. Reetz, G. Mehler, A. Meiswinkel, Tetrahedron: Asymmetry 2004, 15, 2165;
11. d) M. T. Reetz, X. Li, Tetrahedron 2004, 60, 9709;
12. e) M. T. Reetz, X. Li, Angew. Chem. 2005, 117, in press;
13. Angew. Chem. Int. Ed. 2005, in press.
14. a) A. Duursma, R. Hoen, J. Schuppan, R. Hulst, A. J. Minnaard, B. L. Feringa, Org. Lett. 2003, 5, 3111;
15. b) A. Duursma, J.-G. Boiteau, L. Lefort, J. A. F. Boogers, A. H. M. de Vries, J. G. de Vries, A. J. Minnaard, B. L. Feringa, J. Org. Chem. 2004, 69, 8045.
16. a) T. Sturm, W. Weissensteiner, F. Spindler, Adv. Synth. Catal. 2003, 345, 160;
17. b) Y. Yuasa, Y. Yuasa, H. Tsuruta, Can. J. Chem. 1998, 76, 1304;
18. c) A. Dondoni, G. De Lathauwer, D. Perrone, Tetrahedron Lett. 2001, 42, 4819.
19. a) I. Churcher, K. Ashton, J. W. Butcher, E. E. Clarke, H. D. L. Harrison, A. P. Owens, M. R. Teall, S. Williams, J. D. Wrigley, Bioorg. Med. Chem. Lett. 2003, 13, 179;
20. b) A. P. Owens, A. Nadin, A. C. Talbot, E. E. Clarke, T. Harrison, H. D. Lewis, M. Reilly, J. D. J. Wrigley, J. Castro, Bioorg. Med. Chem. Lett. 2003, 13, 4143.
21. Y. Yuasa, Y. Yuasa, H. Tsuruta, Aust. J. Chem. 1998, 51, 511.
22. M. L. Bray, D. Gorbacheva, H. Jahansouz, M. J. Kaufman, K. Ishikawa, N. Harada, K. Suzuki, Chem. Pharm. Bull. 2001, 49, 1.
23. a) Y. Lu, T. M.-D. Nguyen, G. Weltrowska, I. Berezowska, C. Lemieux, N. N. Chung, P. W. Schiller, J. Med. Chem. 2001, 44, 3048;
24. b) Y. Lu, G. Weltrowska, C. Lemieux, N. N. Chung, P. W. Schiller, Bioorg. Med. Chem. Lett. 2001, 11, 323.
25. The beneficial effect of piperidine as the amine moiety in phosphoramidite L1c was also observed in other hydrogenations: H. Bernsmann, M. van den Berg, R. Hoen, G. Mehler, M. T. Reetz, A. J. Minnaard, J. G. de Vries, B. L. Feringa, J. Org. Chem. 2005, 70, 943.
26. 2 pressure, 30°C, and a 2:1 ratio of phosphoramidite and phosphine.
27. For compound 2 see: a) I. Yamada, M. Ohkouchi, M. Yamaguchi, T. J. Yamagishi, J. Chem. Soc. Perkin Trans. 1 1997, 1869;
28. b) T. Uemura, X. Zhang, K Matsumura, N. Sayo, H. Kumobayashi, T. Ohta, K. Nozaki, H. Takaya, J. Org. Chem. 1996, 61, 5510;
29. c) F. Spindler, C. Malan, M. Lotz, M. Kesselgruber, U. Pittelkow, A. Rivas-Nass, O. Briel, H.-U. Blaser, Tetrahedron: Asymmetry 2004, 15, 2299;
30. d) F. Maienza, F. Santoro, F. Spindler, C. Malan, A. Mezzetti, Tetrahedron: Asymmetry 2002, 13, 1817;
31. e) I. Yamada, M. Yamaguchi, T. Yamagishi, Tetrahedron: Asymmetry 1996, 7, 3339;
32. f) X. Cheng, Q. Zhang, J.-H. Xie, L.-X. Wang, Q.-L Zhou, Angew. Chem. 2005, 117, 1142;
33. Angew. Chem. Int. Ed. 2005, 44, 1118.
34. For compound 12 see: a) M. D. Jones, R. Raja, J. M. Thomas, B. F. G. Johnson, D. W. Lewis, J. Rouzad, K. D. M. Harris, Angew. Chem. 2003, 115, 4462;
35. Angew. Chem. Int. Ed. 2003, 42, 4326;
36. b) J. Rouzad, M. D. Jones, R. Raja, B. F. G. Johnson, J. M. Thomas, M. J. Duer, Helv. Chim. Acta 2003, 86, 1753.
37. a) C. J. A. Daley, J. A. Wiles, S. H. Bergens, Can. J. Chem. 1998, 76, 1447;
38. b) J. P. Genêt, C. Pinel, V. Ratovelomanana-Vidal, S. Mallart, X. Pfister, L. Bischoff, M. C. Caño de Andrade, S. Darses, C. Galopin, J. A. Laffitte, Tetrahedron: Asymmetry 1994, 5, 675.
39. The absolute configuration of 11 was confirmed by X-ray analysis of the corresponding α-methylbenzylamine derivative. The absolute configurations of 9 and 10 were assigned by analogy (see Supporting Information).