Rhodium(I) catalyzed asymmetric hydrogenation of enamines

Tetrahedron Letters

Volumn 41, Issue 14, 2000, Pages 2351-2355

  Tararov, Vitali I ^a,b   Kadyrov, Renat ^a   Riermeier, Thomas H ^c   Holz, Jens ^a   Börner, Armin ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^c SANOFI AVENTIS DEUTSCHLAND GMBH   (Germany)

Author keywords

Amines; Asymmetric synthesis; Enamines; Hydrogenation; Rhodium

Indexed keywords

AMINE; ENAMINE; LIGAND; PHOSPHINE DERIVATIVE; RHODIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGENATION; SYNTHESIS;

EID: 0034175642     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00197-0     Document Type: Article

References (35)

1. (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p. 1.
2. (b) Burk, M. J.; Bienewald, F. In Transition Metals for Organic Synthesis; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998; Vol. 2, p. 13.
3. For some recent publications, see: (a) Holz, J.; Heller, D.; Stürmer, R.; Börner, A. Tetrahedron Lett. 1999, 40, 7059. (b) RajanBabu, T. V.; Radetich, B.; You, K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429. (c) Yamanoi, Y.; Imamoto, T. J. Org. Chem. 1999, 64, 2988. (d) Chen, Y.; Li, X.; Tong, S.-k.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 957. (e) Kang, J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523. (f) Almena Perea, J. J.; Börner, A.; Knochel, P. Tetrahedron Lett. 1998, 39, 8073. (g) Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stürmer, R.; Börner, A. J. Org. Chem. 1998, 63, 8031.
4. For some recent publications, see: (a) Holz, J.; Heller, D.; Stürmer, R.; Börner, A. Tetrahedron Lett. 1999, 40, 7059. (b) RajanBabu, T. V.; Radetich, B.; You, K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429. (c) Yamanoi, Y.; Imamoto, T. J. Org. Chem. 1999, 64, 2988. (d) Chen, Y.; Li, X.; Tong, S.-k.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 957. (e) Kang, J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523. (f) Almena Perea, J. J.; Börner, A.; Knochel, P. Tetrahedron Lett. 1998, 39, 8073. (g) Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stürmer, R.; Börner, A. J. Org. Chem. 1998, 63, 8031.
5. For some recent publications, see: (a) Holz, J.; Heller, D.; Stürmer, R.; Börner, A. Tetrahedron Lett. 1999, 40, 7059. (b) RajanBabu, T. V.; Radetich, B.; You, K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429. (c) Yamanoi, Y.; Imamoto, T. J. Org. Chem. 1999, 64, 2988. (d) Chen, Y.; Li, X.; Tong, S.-k.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 957. (e) Kang, J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523. (f) Almena Perea, J. J.; Börner, A.; Knochel, P. Tetrahedron Lett. 1998, 39, 8073. (g) Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stürmer, R.; Börner, A. J. Org. Chem. 1998, 63, 8031.
6. For some recent publications, see: (a) Holz, J.; Heller, D.; Stürmer, R.; Börner, A. Tetrahedron Lett. 1999, 40, 7059. (b) RajanBabu, T. V.; Radetich, B.; You, K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429. (c) Yamanoi, Y.; Imamoto, T. J. Org. Chem. 1999, 64, 2988. (d) Chen, Y.; Li, X.; Tong, S.-k.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 957. (e) Kang, J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523. (f) Almena Perea, J. J.; Börner, A.; Knochel, P. Tetrahedron Lett. 1998, 39, 8073. (g) Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stürmer, R.; Börner, A. J. Org. Chem. 1998, 63, 8031.
7. For some recent publications, see: (a) Holz, J.; Heller, D.; Stürmer, R.; Börner, A. Tetrahedron Lett. 1999, 40, 7059. (b) RajanBabu, T. V.; Radetich, B.; You, K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429. (c) Yamanoi, Y.; Imamoto, T. J. Org. Chem. 1999, 64, 2988. (d) Chen, Y.; Li, X.; Tong, S.-k.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 957. (e) Kang, J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523. (f) Almena Perea, J. J.; Börner, A.; Knochel, P. Tetrahedron Lett. 1998, 39, 8073. (g) Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stürmer, R.; Börner, A. J. Org. Chem. 1998, 63, 8031.
8. For some recent publications, see: (a) Holz, J.; Heller, D.; Stürmer, R.; Börner, A. Tetrahedron Lett. 1999, 40, 7059. (b) RajanBabu, T. V.; Radetich, B.; You, K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429. (c) Yamanoi, Y.; Imamoto, T. J. Org. Chem. 1999, 64, 2988. (d) Chen, Y.; Li, X.; Tong, S.-k.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 957. (e) Kang, J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523. (f) Almena Perea, J. J.; Börner, A.; Knochel, P. Tetrahedron Lett. 1998, 39, 8073. (g) Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stürmer, R.; Börner, A. J. Org. Chem. 1998, 63, 8031.
9. For some recent publications, see: (a) Holz, J.; Heller, D.; Stürmer, R.; Börner, A. Tetrahedron Lett. 1999, 40, 7059. (b) RajanBabu, T. V.; Radetich, B.; You, K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429. (c) Yamanoi, Y.; Imamoto, T. J. Org. Chem. 1999, 64, 2988. (d) Chen, Y.; Li, X.; Tong, S.-k.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 957. (e) Kang, J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523. (f) Almena Perea, J. J.; Börner, A.; Knochel, P. Tetrahedron Lett. 1998, 39, 8073. (g) Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stürmer, R.; Börner, A. J. Org. Chem. 1998, 63, 8031.
10. For recent advances, see e.g.: (a) Zhang, Z.; Zhu, G.; Jiang, Q.; Xiao, D.; Zhang, X. J. Org. Chem. 1999, 64, 1774. (b) Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem. 1998, 63, 6084. (c) Zhu, G.; Zhang, X. J. Org. Chem. 1998, 63, 9590. (d) Tschaen, D. M.; Abramson, L.; Cai, D.; Desmond, R.; Dolling, U.-H.; Frey, L.; Karady, S.; Shi, Y.-J.; Verhoeven, T. R. J. Org. Chem. 1995, 60, 4324. (e) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297.
11. For recent advances, see e.g.: (a) Zhang, Z.; Zhu, G.; Jiang, Q.; Xiao, D.; Zhang, X. J. Org. Chem. 1999, 64, 1774. (b) Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem. 1998, 63, 6084. (c) Zhu, G.; Zhang, X. J. Org. Chem. 1998, 63, 9590. (d) Tschaen, D. M.; Abramson, L.; Cai, D.; Desmond, R.; Dolling, U.-H.; Frey, L.; Karady, S.; Shi, Y.-J.; Verhoeven, T. R. J. Org. Chem. 1995, 60, 4324. (e) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297.
12. For recent advances, see e.g.: (a) Zhang, Z.; Zhu, G.; Jiang, Q.; Xiao, D.; Zhang, X. J. Org. Chem. 1999, 64, 1774. (b) Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem. 1998, 63, 6084. (c) Zhu, G.; Zhang, X. J. Org. Chem. 1998, 63, 9590. (d) Tschaen, D. M.; Abramson, L.; Cai, D.; Desmond, R.; Dolling, U.-H.; Frey, L.; Karady, S.; Shi, Y.-J.; Verhoeven, T. R. J. Org. Chem. 1995, 60, 4324. (e) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297.
13. For recent advances, see e.g.: (a) Zhang, Z.; Zhu, G.; Jiang, Q.; Xiao, D.; Zhang, X. J. Org. Chem. 1999, 64, 1774. (b) Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem. 1998, 63, 6084. (c) Zhu, G.; Zhang, X. J. Org. Chem. 1998, 63, 9590. (d) Tschaen, D. M.; Abramson, L.; Cai, D.; Desmond, R.; Dolling, U.-H.; Frey, L.; Karady, S.; Shi, Y.-J.; Verhoeven, T. R. J. Org. Chem. 1995, 60, 4324. (e) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297.
14. For recent advances, see e.g.: (a) Zhang, Z.; Zhu, G.; Jiang, Q.; Xiao, D.; Zhang, X. J. Org. Chem. 1999, 64, 1774. (b) Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem. 1998, 63, 6084. (c) Zhu, G.; Zhang, X. J. Org. Chem. 1998, 63, 9590. (d) Tschaen, D. M.; Abramson, L.; Cai, D.; Desmond, R.; Dolling, U.-H.; Frey, L.; Karady, S.; Shi, Y.-J.; Verhoeven, T. R. J. Org. Chem. 1995, 60, 4324. (e) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297.
15. Halpern, J. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1985; p. 41.
16. For a review, see: Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
17. Tararov, V. I.; Kadyrov, R.; Riermeier, T. H.; Holz, J.; Börner, A. Tetrahedron: Asymmetry 1999, 10, 4009.
18. (a) Lee, N. E.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 5985.
19. (b) Spindler, F.; Blaser, H.-U. In Transition Metals for Organic Synthesis; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998; Vol. 2, p. 69.
20. 2 as a catalyst: Rische, T.; Rzychon-Kitsos, B.; Eilbracht, P. Tetrahedron 1998, 54, 2723.
21. Achiwa, K. J. Am. Chem. Soc. 1976, 98, 8265.
22. Kagan, H. B.; Dang, T. P. J. Am. Chem. Soc. 1972, 94, 6429.
23. Holz, J.; Börner, A. Unpublished.
24. Berens, U.; Leckel, D.; Oepen, S. C. J. Org. Chem. 1995, 60, 8294.
25. (a) Kumar, A.; Oehme, G.; Roque, J. P.; Schwarze, M.; Selke, R. Angew. Chem. 1994, 106, 2272; Angew. Chem., Int. Ed. Engl. 1994, 33, 2197.
26. Angew. Chem., Int. Ed. Engl. 1994, 33, 2197.
27. (b) Selke, R.; Ohff, M.; Riepe, A. Tetrahedron 1996, 52, 15079.
28. Tanaka, M.; Ogata, I. J. Chem. Soc., Chem. Commun. 1975, 735.
29. These ligands revealed to be superior among ca. 30 Rh(I) and Ir(I) diphosphine and diphosphinite complexes screened. Due to poor hydrogenation activity observed and the production of racemic product the values obtained with these complexes are not detailed in this preliminary publication.
30. 3, (R)-enantiomer), 4.29 (q, J=6.9 Hz, CH, (S)-enantiomer), 4.30 (q, J=6.9 Hz, CH, (R)-enantiomer). 2-N-Piperidinylethylbenzene decomposed rather fast under red colouring.
31. Yurovskaya, M. A.; Karchava, A. V. Tetrahedron: Asymmetry 1998, 9, 3331 and references cited therein.
32. Seklyaev, V. S.; Aleksandrov, B. B.; Gavrilov, M. S.; Mikhailoskii, A. G.; Vakhrin, M. I. Khim. Geterothsikl. Soedin. 1988, 937.
33. Shinmori, H.; Takeuchi, M.; Shinkai, S. J. Chem. Soc., Perkin 2, 1966, 1.
34. -3 mbar, m.p. 63-64°C (hexane). The compound should be stored under Ar to prevent fast red colouring.
35. 3, enantiomer A). Enantiomer A was formed in excess in the hydrogenation with [(R,R)-bdpch] as ligand.