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Volumn 64, Issue 26, 1999, Pages 9381-9385

Highly enantioselective hydrogenation of enamides and itaconic acid in water in the presence of water-soluble rhodium(I) catalyst and sodium dodecyl sulfate

Author keywords

[No Author keywords available]

Indexed keywords

DODECYL SULFATE SODIUM; ITACONIC ACID; RHODIUM;

EID: 0033601295     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9912505     Document Type: Article
Times cited : (89)

References (67)
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    • The derivatization of monosaccharide and α,α,-trehalose for the synthesis of chiral ligands and their application to asymmetric reactions have been reported. For examples, see: (a) RajanBabu, T. V.; Radetich, B.; You, K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429. (b) Yonehara, K.; Hashizume, T.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1998, 71, 1967. (c) Boog- Wick, K.; Pregosin, P. S.; Wörle, M.; Albinati, A. Helv. Chim. Acta 1998, 81, 1622. (d) RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. (e) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. Adv. Catal. Proc. 1997, 2, 1. (f) Berens, U.; Selke, R. Tetrahedron: Asymmetry 1996, 7, 2055. (g) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1995, 60, 6226. (h) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (i) Selke, R.; Facklam, C.; Foken, H.; Heller, D. Tetrahedron: Asymmetry 1993, 4, 369. (j) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. (k) Selke, R. J. Organomet. Chem. 1989, 370, 249. (l) Brown, J. M.; Cook, S. J.; Khan, R. Tetrahedron 1986, 42, 5105. (m) Selke, R.; Pracejus, H. J. Mol. Catal. 1986, 37, 213. (n) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (o) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635.
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    • The derivatization of monosaccharide and α,α,-trehalose for the synthesis of chiral ligands and their application to asymmetric reactions have been reported. For examples, see: (a) RajanBabu, T. V.; Radetich, B.; You, K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429. (b) Yonehara, K.; Hashizume, T.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1998, 71, 1967. (c) Boog- Wick, K.; Pregosin, P. S.; Wörle, M.; Albinati, A. Helv. Chim. Acta 1998, 81, 1622. (d) RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. (e) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. Adv. Catal. Proc. 1997, 2, 1. (f) Berens, U.; Selke, R. Tetrahedron: Asymmetry 1996, 7, 2055. (g) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1995, 60, 6226. (h) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (i) Selke, R.; Facklam, C.; Foken, H.; Heller, D. Tetrahedron: Asymmetry 1993, 4, 369. (j) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. (k) Selke, R. J. Organomet. Chem. 1989, 370, 249. (l) Brown, J. M.; Cook, S. J.; Khan, R. Tetrahedron 1986, 42, 5105. (m) Selke, R.; Pracejus, H. J. Mol. Catal. 1986, 37, 213. (n) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (o) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635.
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    • The derivatization of monosaccharide and α,α,-trehalose for the synthesis of chiral ligands and their application to asymmetric reactions have been reported. For examples, see: (a) RajanBabu, T. V.; Radetich, B.; You, K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429. (b) Yonehara, K.; Hashizume, T.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1998, 71, 1967. (c) Boog- Wick, K.; Pregosin, P. S.; Wörle, M.; Albinati, A. Helv. Chim. Acta 1998, 81, 1622. (d) RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. (e) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. Adv. Catal. Proc. 1997, 2, 1. (f) Berens, U.; Selke, R. Tetrahedron: Asymmetry 1996, 7, 2055. (g) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1995, 60, 6226. (h) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (i) Selke, R.; Facklam, C.; Foken, H.; Heller, D. Tetrahedron: Asymmetry 1993, 4, 369. (j) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. (k) Selke, R. J. Organomet. Chem. 1989, 370, 249. (l) Brown, J. M.; Cook, S. J.; Khan, R. Tetrahedron 1986, 42, 5105. (m) Selke, R.; Pracejus, H. J. Mol. Catal. 1986, 37, 213. (n) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (o) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635.
    • (1986) Tetrahedron , vol.42 , pp. 5105
    • Brown, J.M.1    Cook, S.J.2    Khan, R.3
  • 51
    • 0022791840 scopus 로고
    • The derivatization of monosaccharide and α,α,-trehalose for the synthesis of chiral ligands and their application to asymmetric reactions have been reported. For examples, see: (a) RajanBabu, T. V.; Radetich, B.; You, K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429. (b) Yonehara, K.; Hashizume, T.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1998, 71, 1967. (c) Boog- Wick, K.; Pregosin, P. S.; Wörle, M.; Albinati, A. Helv. Chim. Acta 1998, 81, 1622. (d) RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. (e) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. Adv. Catal. Proc. 1997, 2, 1. (f) Berens, U.; Selke, R. Tetrahedron: Asymmetry 1996, 7, 2055. (g) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1995, 60, 6226. (h) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (i) Selke, R.; Facklam, C.; Foken, H.; Heller, D. Tetrahedron: Asymmetry 1993, 4, 369. (j) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. (k) Selke, R. J. Organomet. Chem. 1989, 370, 249. (l) Brown, J. M.; Cook, S. J.; Khan, R. Tetrahedron 1986, 42, 5105. (m) Selke, R.; Pracejus, H. J. Mol. Catal. 1986, 37, 213. (n) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (o) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635.
    • (1986) J. Mol. Catal. , vol.37 , pp. 213
    • Selke, R.1    Pracejus, H.2
  • 52
    • 0002239799 scopus 로고
    • The derivatization of monosaccharide and α,α,-trehalose for the synthesis of chiral ligands and their application to asymmetric reactions have been reported. For examples, see: (a) RajanBabu, T. V.; Radetich, B.; You, K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429. (b) Yonehara, K.; Hashizume, T.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1998, 71, 1967. (c) Boog- Wick, K.; Pregosin, P. S.; Wörle, M.; Albinati, A. Helv. Chim. Acta 1998, 81, 1622. (d) RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. (e) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. Adv. Catal. Proc. 1997, 2, 1. (f) Berens, U.; Selke, R. Tetrahedron: Asymmetry 1996, 7, 2055. (g) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1995, 60, 6226. (h) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (i) Selke, R.; Facklam, C.; Foken, H.; Heller, D. Tetrahedron: Asymmetry 1993, 4, 369. (j) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. (k) Selke, R. J. Organomet. Chem. 1989, 370, 249. (l) Brown, J. M.; Cook, S. J.; Khan, R. Tetrahedron 1986, 42, 5105. (m) Selke, R.; Pracejus, H. J. Mol. Catal. 1986, 37, 213. (n) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (o) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635.
    • (1978) J. Organomet. Chem. , vol.159
    • Jackson, R.1    Thompson, D.J.2
  • 53
    • 0001080719 scopus 로고
    • The derivatization of monosaccharide and α,α,-trehalose for the synthesis of chiral ligands and their application to asymmetric reactions have been reported. For examples, see: (a) RajanBabu, T. V.; Radetich, B.; You, K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429. (b) Yonehara, K.; Hashizume, T.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1998, 71, 1967. (c) Boog- Wick, K.; Pregosin, P. S.; Wörle, M.; Albinati, A. Helv. Chim. Acta 1998, 81, 1622. (d) RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. (e) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. Adv. Catal. Proc. 1997, 2, 1. (f) Berens, U.; Selke, R. Tetrahedron: Asymmetry 1996, 7, 2055. (g) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1995, 60, 6226. (h) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (i) Selke, R.; Facklam, C.; Foken, H.; Heller, D. Tetrahedron: Asymmetry 1993, 4, 369. (j) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. (k) Selke, R. J. Organomet. Chem. 1989, 370, 249. (l) Brown, J. M.; Cook, S. J.; Khan, R. Tetrahedron 1986, 42, 5105. (m) Selke, R.; Pracejus, H. J. Mol. Catal. 1986, 37, 213. (n) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (o) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635.
    • (1978) Tetrahedron Lett. , pp. 1635
    • Cullen, W.R.1    Sugi, Y.2
  • 55
    • 0000624635 scopus 로고    scopus 로고
    • (b) Recently, RajanBabu and co-worker have independently reported the synthesis of water-soluble chiral Rh complex from α,α-trehalose. See: Shin, S.; RajanBabu, T. V. Org. Lett. 1999, 1, 1229.
    • (1999) Org. Lett. , vol.1 , pp. 1229
    • Shin, S.1    RajanBabu, T.V.2
  • 63
    • 0342658219 scopus 로고    scopus 로고
    • note
    • 4 in degassed THF under Ar at room temperature for 1 h.
  • 64
    • 0343092498 scopus 로고    scopus 로고
    • note
    • 5a in degassed THF under Ar was treated with 80% aqueous TfOH or D-camphor-10-sulfonic acid at room temperature for 1 h to give a cationic water-soluble rhodium complex [Rh(α-D-glucopyranosyl-(1,1)-2,3-di-O-(diphenylphosphino)-α-D- glucopyranoside)(cod)]OTf(6)or [Rh(β-D-glucopyranosyl-(1,1)-2,3-di-O-(diphenylphospnino)-β-D- glucopyranoside)(cod)]-D-camphor-10-sulfonate (7).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.