Industrial synthesis of (+)-cis-methyl dihydrojasmonate by enantioselective catalytic hydrogenation; identification of the precatalyst [Ru((-)-Me-DuPHOS)(H)(η6-1,3,5-cyclooctatriene)](BF4)

Angewandte Chemie - International Edition

Volumn 39, Issue 11, 2000, Pages 1992-1995

  Dobbs, Daniel A ^a   Vanhessche, Koenraad P M ^a   Brazi, Eric ^a   Rautenstrauch, Valentin ^a   Lenoir, Jean Yves ^b   Genêt, Jean Pierre ^b   Wiles, Jason ^d   Bergens, Steven H ^c  

^a Email:   (Switzerland)

^b PSL RESEARCH UNIVERSITY   (France)

^c UNIVERSITY OF ALBERTA   (Canada)

^d NONE

Author keywords

Asymmetric catalysis; Homogenous catalysis; Hydrogenations; Precatalysts; Ruthenium

Indexed keywords

JASMONIC ACID;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; HYDROGENATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034595793     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000602)39:11<1992::AID-ANIE1992>3.0.CO;2-W     Document Type: Article

References (68)

1. a) Reviews: T. K. Sarkar, B. K. Ghorai, J. Indian Chem. Soc. 1999, 76, 693-706;
2. b) F. Schröder, Angew. Chem. 1998, 110, 1271-1274; Angew. Chem. Int. Ed. 1998, 37, 1213-1216;
3. b) F. Schröder, Angew. Chem. 1998, 110, 1271-1274; Angew. Chem. Int. Ed. 1998, 37, 1213-1216;
4. c) M. H. Beale, J. L. Ward, Nat. Prod. Rep. 1998, 433-548;
5. d) G. Sembdner, P. Parthier, Annu. Rev. Plant Physiol. Plant Mol. Biol. 1993, 44, 569-589;
6. e) M. Hamberg, H. W. Gardner, Biochem. Biophys. Acta 1992, 1165, 1-18.
7. See also: f) W. Boland, J. Hopke, J. Donath, J. Nüske, F. Bublitz, Angew. Chem. 1995, 107, 1715-1717; Angew. Chem. Int. Ed. Engl. 1995, 34, 1600-1602.
8. See also: f) W. Boland, J. Hopke, J. Donath, J. Nüske, F. Bublitz, Angew. Chem. 1995, 107, 1715-1717; Angew. Chem. Int. Ed. Engl. 1995, 34, 1600-1602.
9. Compound (-)-2 was at first thought to be the primary natural product and responsible for the odor, and therefore named methyl jasmonate. Later, (+)-1 was found to be both the primary product and the biologically active and odorant compound, and named methyl epijasmonale. For simplicity, we name as follows: (+)-cis-methyl jasmonate (+)-1, (-)-trans-methyl jasmonate (-)-2, (+)-cis-methyl dihydrojasmonate (+)-3, (-)-trans-methyl dihydrojasmonate (-)-4.
10. T. E. Acree, R. Nishida, H. Fukami, J. Agric. Food Chem. 1985, 33, 425-427; R. Nishida, T.E. Acree, H. Fukami, Agric. Biol. Chem. 1985, 49, 769-772.
11. T. E. Acree, R. Nishida, H. Fukami, J. Agric. Food Chem. 1985, 33, 425-427; R. Nishida, T.E. Acree, H. Fukami, Agric. Biol. Chem. 1985, 49, 769-772.
12. G. Ohloff, Scent and Fragrances, Springer, Berlin, 1994, pp. 151-154; G. Fráter, J. A. Bajgrowicz, P. Kraft, Tetrahedron 1998, 54, 7633-7703.
13. G. Ohloff, Scent and Fragrances, Springer, Berlin, 1994, pp. 151-154; G. Fráter, J. A. Bajgrowicz, P. Kraft, Tetrahedron 1998, 54, 7633-7703.
14. a) E. Demole, E. Lederer, D. Mercier, Helv. Chim. Acta 1962, 45, 675-685;
15. b) E. Demole, E. Lederer, D. Mercier, Helv. Chim. Acta 1962, 45, 685-692;
16. c) E. Demole, M. Stoll, Helv. Chim. Acta 1962, 45, 692-703.
17. For an important early review, see: d) E. Demole in Fragrance Chemistry (Ed.: E. T. Theimer), Academic Press, New York, 1982, pp. 349-396.
18. [1a, 5d]; (±)-1: a) M. Sannigrahi, D. L. Mayhew, D. L. J. Clive, J. Org. Chem. 1999, 64, 2776-2788;
19. b) T. K. Sarkar, B. K. Ghorai, S. K. Nandy, B. Mukherjee, A. Banerji, J. Org. Chem. 1997, 62, 6006-6011;
20. c) T. K. Sarkar, B. K. Ghorai, A. Banerji, Tetrahedron Lett. 1994, 35, 6907-6909;
21. d) G. Stork, O. Ouerfelli, New J. Chem. 1992, 16, 95-98;
22. e) T. Kitahara, Y. Warita, M. Abe, M. Seya, Y. Takagi, K. Mori, Agric. Biol. Chem. 1991, 55, 1013-1017;
23. f) L. Crombie, K.M. Mistry, J. Chem. Soc. Perkin 1 1991, 1981-1991;
24. g) H. Seto, H. Yoshioka, Chem. Lett. 1990, 1797-1800;
25. h) L. Crombie, K.M. Mistry, J. Chem. Soc. Chem. Commun. 1988, 539-540;
26. i) T. Kitahara, K. Miura, Y. Warita, Y. Takagi, K. Mori, Agric. Biol. Chem. 1987, 51, 1129-1133;
27. j) R. V. Stevens, N. Hrib, Tetrahedron Lett. 1981, 22, 4791-4794;
28. k) H. Tanaka, S. Torii, J. Org. Chem. 1975, 40, 462-465. (+)-1:
29. l) C. Fehr, J. Galindo, Angew. Chem. 2000, 112, 581-585; Angew. Chem. Int. Ed. 2000, 39, 569-573;
30. (+)-1: l) C. Fehr, J. Galindo, Angew. Chem. 2000, 112, 581-585; Angew. Chem. Int. Ed. 2000, 39, 569-573;
31. m) T. K. Sarkar, B. Mukherjee, S. K. Gosh, Tetrahedron 1998, 54, 3243-3254;
32. n) G. J. Roth, S. Kirschbaum, H. J. Bestmann, Synlett 1997, 618-620;
33. o) H. Stadtmüller, A. Vaupel, C. E. Tucker, T. Stüdemann, P. Knochel, Chem. Eur. J. 1996, 2, 1204-1220;
34. p) H. Stadtmüller, P. Knochel, Synlett 1995, 463-464;
35. q) T. Kitahara, T. Nishi, K. Mori, Tetrahedron 1991, 47, 6999-7006;
36. r) G. Helmchen, A. Goeke, G. Lauer, M. Urmann, J. Fries. Angew. Chem. 1990, 102, 1079-1080; Angew. Chem. Int. Ed. Engl. 1990, 29, 1024-1025;
37. r) G. Helmchen, A. Goeke, G. Lauer, M. Urmann, J. Fries. Angew. Chem. 1990, 102, 1079-1080; Angew. Chem. Int. Ed. Engl. 1990, 29, 1024-1025;
38. s) K. Weinges, U. Lernhardt, Liebigs Ann. Chem. 1990, 751-754.
39. O. Miersch, R. Kramell, B. Parthier, C. Wasternack, Phytochemistry 1999, 50, 353-361; M. C. S. Cano, E. G. Plaza, R. G. Muñoz, A. G. Benavente, J. Essent. Oil Res. 1998, 10, 67-69; A. S. C. Sing, J. Barbier, J. Smadja, J. Nat. 1997, 9, 8-16; G. Buchbauer, L. Jirovetz, V. K. Kaul, J. Essent. Oil Res. 1995, 7, 5-9; O. Miersch, G. Sembdner, K. Schreiber, Phytochemistry 1989, 28, 339-340: O. Miersch, A. Preiss, G. Sembdner, K. Schreiber, Phytochemistry 1987, 26, 1037-1039: W. Renold, R. Näf-Müller, U Keller, B. Willhalm, G. Ohloff, Helv. Chim. Acta 1974, 57, 1301-1308.
40. O. Miersch, R. Kramell, B. Parthier, C. Wasternack, Phytochemistry 1999, 50, 353-361; M. C. S. Cano, E. G. Plaza, R. G. Muñoz, A. G. Benavente, J. Essent. Oil Res. 1998, 10, 67-69; A. S. C. Sing, J. Barbier, J. Smadja, J. Nat. 1997, 9, 8-16; G. Buchbauer, L. Jirovetz, V. K. Kaul, J. Essent. Oil Res. 1995, 7, 5-9; O. Miersch, G. Sembdner, K. Schreiber, Phytochemistry 1989, 28, 339-340: O. Miersch, A. Preiss, G. Sembdner, K. Schreiber, Phytochemistry 1987, 26, 1037-1039: W. Renold, R. Näf-Müller, U Keller, B. Willhalm, G. Ohloff, Helv. Chim. Acta 1974, 57, 1301-1308.
41. O. Miersch, R. Kramell, B. Parthier, C. Wasternack, Phytochemistry 1999, 50, 353-361; M. C. S. Cano, E. G. Plaza, R. G. Muñoz, A. G. Benavente, J. Essent. Oil Res. 1998, 10, 67-69; A. S. C. Sing, J. Barbier, J. Smadja, J. Nat. 1997, 9, 8-16; G. Buchbauer, L. Jirovetz, V. K. Kaul, J. Essent. Oil Res. 1995, 7, 5-9; O. Miersch, G. Sembdner, K. Schreiber, Phytochemistry 1989, 28, 339-340: O. Miersch, A. Preiss, G. Sembdner, K. Schreiber, Phytochemistry 1987, 26, 1037-1039: W. Renold, R. Näf-Müller, U Keller, B. Willhalm, G. Ohloff, Helv. Chim. Acta 1974, 57, 1301-1308.
42. O. Miersch, R. Kramell, B. Parthier, C. Wasternack, Phytochemistry 1999, 50, 353-361; M. C. S. Cano, E. G. Plaza, R. G. Muñoz, A. G. Benavente, J. Essent. Oil Res. 1998, 10, 67-69; A. S. C. Sing, J. Barbier, J. Smadja, J. Nat. 1997, 9, 8-16; G. Buchbauer, L. Jirovetz, V. K. Kaul, J. Essent. Oil Res. 1995, 7, 5-9; O. Miersch, G. Sembdner, K. Schreiber, Phytochemistry 1989, 28, 339-340: O. Miersch, A. Preiss, G. Sembdner, K. Schreiber, Phytochemistry 1987, 26, 1037-1039: W. Renold, R. Näf-Müller, U Keller, B. Willhalm, G. Ohloff, Helv. Chim. Acta 1974, 57, 1301-1308.
43. O. Miersch, R. Kramell, B. Parthier, C. Wasternack, Phytochemistry 1999, 50, 353-361; M. C. S. Cano, E. G. Plaza, R. G. Muñoz, A. G. Benavente, J. Essent. Oil Res. 1998, 10, 67-69; A. S. C. Sing, J. Barbier, J. Smadja, J. Nat. 1997, 9, 8-16; G. Buchbauer, L. Jirovetz, V. K. Kaul, J. Essent. Oil Res. 1995, 7, 5-9; O. Miersch, G. Sembdner, K. Schreiber, Phytochemistry 1989, 28, 339-340: O. Miersch, A. Preiss, G. Sembdner, K. Schreiber, Phytochemistry 1987, 26, 1037-1039: W. Renold, R. Näf-Müller, U Keller, B. Willhalm, G. Ohloff, Helv. Chim. Acta 1974, 57, 1301-1308.
44. O. Miersch, R. Kramell, B. Parthier, C. Wasternack, Phytochemistry 1999, 50, 353-361; M. C. S. Cano, E. G. Plaza, R. G. Muñoz, A. G. Benavente, J. Essent. Oil Res. 1998, 10, 67-69; A. S. C. Sing, J. Barbier, J. Smadja, J. Nat. 1997, 9, 8-16; G. Buchbauer, L. Jirovetz, V. K. Kaul, J. Essent. Oil Res. 1995, 7, 5-9; O. Miersch, G. Sembdner, K. Schreiber, Phytochemistry 1989, 28, 339-340: O. Miersch, A. Preiss, G. Sembdner, K. Schreiber, Phytochemistry 1987, 26, 1037-1039: W. Renold, R. Näf-Müller, U Keller, B. Willhalm, G. Ohloff, Helv. Chim. Acta 1974, 57, 1301-1308.
45. O. Miersch, R. Kramell, B. Parthier, C. Wasternack, Phytochemistry 1999, 50, 353-361; M. C. S. Cano, E. G. Plaza, R. G. Muñoz, A. G. Benavente, J. Essent. Oil Res. 1998, 10, 67-69; A. S. C. Sing, J. Barbier, J. Smadja, J. Nat. 1997, 9, 8-16; G. Buchbauer, L. Jirovetz, V. K. Kaul, J. Essent. Oil Res. 1995, 7, 5-9; O. Miersch, G. Sembdner, K. Schreiber, Phytochemistry 1989, 28, 339-340: O. Miersch, A. Preiss, G. Sembdner, K. Schreiber, Phytochemistry 1987, 26, 1037-1039: W. Renold, R. Näf-Müller, U Keller, B. Willhalm, G. Ohloff, Helv. Chim. Acta 1974, 57, 1301-1308.
46. 3 at -75 °C gives (-)-4and (+)-4.
47. 3 at -75 °C gives (-)-4and (+)-4.
48. [61]
49. [61]
50. P. Oberhänsli (Givaudan SA), DO 2008833, 1969 [Chem. Abstr. 1970, 73, 109364e].
51. M. O. Albers, E. Singleton, J. E. Yates, Inorg. Synth. 1989, 26, 249-258.
52. 2O probably codistill).
53. a) J.-P. Genêt, S. Mallart, C. Pinel, S. Juge, J. A. Laffitte, Tetrahedron: Asymmetry 1991, 2, 43-46;
54. b) J.-P. Genêt, C. Pinel, V. Ratovelomanana-Vidal, S. Mallart, X. Pfister, M. C. Caño De Andrade, J. A. Laffitte, Tetrahedron: Asymmetry 1994, 5, 665-674;
55. c) 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, 675-690;
56. d) J.-P. Genêt, Acros Chimica Acta 1994, 1, 1 -8;
57. e) J.-P. Genêt, V. Ratovelomanana-Vidal, M. C. Caño De Andrade, X. Pfister, P. Guerreiro, J.-Y. Lenoir, Tetrahedron Lett. 1995, 36, 4801-4804;
58. f) C. Girard, J.-P. Genêt, M. Bulliard, Eur. J Org. Chem. 1999, 2937-2942.
59. B. Heiser, E. A. Broger, Y. Crameri, Tetrahedron: Asymmetry 1991, 2, 51-62.
60. (-)-Me-DuPHOS (-)-7 = (-)-1,2-bis((2R,5R)2,5-dimethylphospholanyl)benzene; M. J. Burk, J. E. Feaster, W. A. Nugent, R. L. Harlow, J. Am. Chem. Soc. 1993, 115, 10125-10138.
61. (-)-JOSIPHOS (-)-8 = (-)-(R-(1)-[(S)-2-(diphenylphosphanyl)ferrocenyl|ethyldicyclohexylphosphane; A. Togni, C. Breutel, A. Schnyder, F. Spindler, H. Landert, A. Tijani, J. Am. Chem. Soc. 1994, 116, 4062-4066.
62. (-)-9 = (-)-(R)-(1)-[(S)-2-(di(4-trifluoromethylphenyl)phosphanyl)-ferrocenyl] ethyldicyclohexylphosphane; F. Spindler (Ciba-Geigy AG), EP 646590, 1995 [Chem. Abstr. 1995, 123, 112416e].
63. (+)-(R)-BINAP = (+)-(R)-2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl; A. Myashita, A. Yasuda, H. Takaya, K. Toriumi, T. Ito, T. Souchi, R. Noyori, J. Am. Chem. Soc. 1980, 102, 7932-7934.
64. 4 was determined by X-ray diffraction. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-138771. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
65. K. P. M. Vanhessche, D. A. Dobbs, V. Rautenstrauch, J. Wiles, S. H. Bergens, unpublished results.
66. J. A. Wiles, C. E. Lee, R. McDonald, S. H. Bergens, Organometallics 1996, 15, 3782-3784.
67. pp = 30.5 Hz).
68. 31P NMR.