메뉴 건너뛰기




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

Rhodium(I) catalyzed asymmetric hydrogenation of enamines

Author keywords

Amines; Asymmetric synthesis; Enamines; Hydrogenation; Rhodium

Indexed keywords

AMINE; ENAMINE; LIGAND; PHOSPHINE DERIVATIVE; RHODIUM;

EID: 0034175642     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00197-0     Document Type: Article
Times cited : (69)

References (35)
  • 3
    • 0033600689 scopus 로고    scopus 로고
    • For some recent publications, see: (a)
    • 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.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 7059
    • Holz, J.1    Heller, D.2    Stürmer, R.3    Börner, A.4
  • 4
    • 0032933755 scopus 로고    scopus 로고
    • (b)
    • 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.
    • (1999) J. Org. Chem. , vol.64 , pp. 3429
    • Rajanbabu, T.V.1    Radetich, B.2    You, K.K.3    Ayers, T.A.4    Casalnuovo, A.L.5    Calabrese, J.C.6
  • 5
    • 0033617302 scopus 로고    scopus 로고
    • (c)
    • 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.
    • (1999) J. Org. Chem. , vol.64 , pp. 2988
    • Yamanoi, Y.1    Imamoto, T.2
  • 6
    • 0033613696 scopus 로고    scopus 로고
    • (d)
    • 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.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 957
    • Chen, Y.1    Li, X.2    Tong, S.-K.3    Choi, M.C.K.4    Chan, A.S.C.5
  • 7
    • 0032581486 scopus 로고    scopus 로고
    • (e)
    • 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.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 5523
    • Kang, J.1    Lee, J.H.2    Ahn, S.H.3    Choi, J.S.4
  • 8
    • 0032578890 scopus 로고    scopus 로고
    • (f)
    • 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.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 8073
    • Almena Perea, J.J.1    Börner, A.2    Knochel, P.3
  • 9
    • 0001296673 scopus 로고    scopus 로고
    • (g)
    • 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.
    • (1998) J. Org. Chem. , vol.63 , pp. 8031
    • Holz, J.1    Quirmbach, M.2    Schmidt, U.3    Heller, D.4    Stürmer, R.5    Börner, A.6
  • 10
    • 0033583169 scopus 로고    scopus 로고
    • For recent advances, see e.g.: (a)
    • 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.
    • (1999) J. Org. Chem. , vol.64 , pp. 1774
    • Zhang, Z.1    Zhu, G.2    Jiang, Q.3    Xiao, D.4    Zhang, X.5
  • 11
    • 0000489118 scopus 로고    scopus 로고
    • (b)
    • 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.
    • (1998) J. Org. Chem. , vol.63 , pp. 6084
    • Burk, M.J.1    Casy, G.2    Johnson, N.B.3
  • 12
    • 0032509396 scopus 로고    scopus 로고
    • (c)
    • 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.
    • (1998) J. Org. Chem. , vol.63 , pp. 9590
    • Zhu, G.1    Zhang, X.2
  • 13
    • 0029153568 scopus 로고
    • (d)
    • 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.
    • (1995) J. Org. Chem. , vol.60 , pp. 4324
    • Tschaen, D.M.1    Abramson, L.2    Cai, D.3    Desmond, R.4    Dolling, U.-H.5    Frey, L.6    Karady, S.7    Shi, Y.-J.8    Verhoeven, T.R.9
  • 14
    • 0028330928 scopus 로고
    • (e)
    • 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.
    • (1994) J. Org. Chem. , vol.59 , pp. 297
    • Kitamura, M.1    Hsiao, Y.2    Ohta, M.3    Tsukamoto, M.4    Ohta, T.5    Takaya, H.6    Noyori, R.7
  • 15
    • 84941207091 scopus 로고
    • Morrison, J. D., Ed.; Academic Press: Orlando
    • Halpern, J. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1985; p. 41.
    • (1985) In Asymmetric Synthesis , pp. 41
    • Halpern, J.1
  • 29
    • 0343230119 scopus 로고    scopus 로고
    • 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
    • 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
    • 0342360591 scopus 로고    scopus 로고
    • 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
    • 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.
  • 34
    • 0342795523 scopus 로고    scopus 로고
    • -3 mbar, m.p. 63-64°C (hexane). The compound should be stored under Ar to prevent fast red colouring.
    • -3 mbar, m.p. 63-64°C (hexane). The compound should be stored under Ar to prevent fast red colouring.
  • 35
    • 0342360590 scopus 로고    scopus 로고
    • 3, enantiomer A). Enantiomer A was formed in excess in the hydrogenation with [(R,R)-bdpch] as ligand.
    • 3, enantiomer A). Enantiomer A was formed in excess in the hydrogenation with [(R,R)-bdpch] as ligand.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.