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Volumn 346, Issue 9-10, 2004, Pages 1220-1230

Aza-Baylis-Hillman reaction of β-substituted activated olefins with N-tosyl imines

Author keywords

Aza Baylis Hillman reaction; Enones; Lewis base catalyst; N tosyl imines; Organic catalysis; Phosphanes

Indexed keywords

2 HEXENAL; ALKENE DERIVATIVE; CROTONALDEHYDE; IMINE; KETONE DERIVATIVE; PHOSPHINE;

EID: 5144223349     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404045     Document Type: Article
Times cited : (41)

References (33)
  • 1
    • 0342419508 scopus 로고    scopus 로고
    • For reviews, see: a) D. Basavaiah, P. D. Rao, R. S. Hyma, Tetrahedron 1996, 52, 8001-8062; b) S. E. Drewes, G. H. P. Roo, Tetrahedron 1988, 44, 4653-4670; c) E. Ciganek, Org. React. 1997, 51, 201-350; d) P. Langer, Angew. Chem. Int. Ed. 2000, 39, 3049-3052; e) E. Ciganek, Org. React. 1997, 51, 201-350; f) D. Basavaiah, A. J. Rao, T. Satyanarayana, Chem. Rev. 2003, 103, 811-892.
    • (1996) Tetrahedron , vol.52 , pp. 8001-8062
    • Basavaiah, D.1    Rao, P.D.2    Hyma, R.S.3
  • 2
    • 4744362831 scopus 로고
    • For reviews, see: a) D. Basavaiah, P. D. Rao, R. S. Hyma, Tetrahedron 1996, 52, 8001-8062; b) S. E. Drewes, G. H. P. Roo, Tetrahedron 1988, 44, 4653-4670; c) E. Ciganek, Org. React. 1997, 51, 201-350; d) P. Langer, Angew. Chem. Int. Ed. 2000, 39, 3049-3052; e) E. Ciganek, Org. React. 1997, 51, 201-350; f) D. Basavaiah, A. J. Rao, T. Satyanarayana, Chem. Rev. 2003, 103, 811-892.
    • (1988) Tetrahedron , vol.44 , pp. 4653-4670
    • Drewes, S.E.1    Roo, G.H.P.2
  • 3
    • 0000892247 scopus 로고    scopus 로고
    • For reviews, see: a) D. Basavaiah, P. D. Rao, R. S. Hyma, Tetrahedron 1996, 52, 8001-8062; b) S. E. Drewes, G. H. P. Roo, Tetrahedron 1988, 44, 4653-4670; c) E. Ciganek, Org. React. 1997, 51, 201-350; d) P. Langer, Angew. Chem. Int. Ed. 2000, 39, 3049-3052; e) E. Ciganek, Org. React. 1997, 51, 201-350; f) D. Basavaiah, A. J. Rao, T. Satyanarayana, Chem. Rev. 2003, 103, 811-892.
    • (1997) Org. React. , vol.51 , pp. 201-350
    • Ciganek, E.1
  • 4
    • 0034283585 scopus 로고    scopus 로고
    • For reviews, see: a) D. Basavaiah, P. D. Rao, R. S. Hyma, Tetrahedron 1996, 52, 8001-8062; b) S. E. Drewes, G. H. P. Roo, Tetrahedron 1988, 44, 4653-4670; c) E. Ciganek, Org. React. 1997, 51, 201-350; d) P. Langer, Angew. Chem. Int. Ed. 2000, 39, 3049-3052; e) E. Ciganek, Org. React. 1997, 51, 201-350; f) D. Basavaiah, A. J. Rao, T. Satyanarayana, Chem. Rev. 2003, 103, 811-892.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3049-3052
    • Langer, P.1
  • 5
    • 0000892247 scopus 로고    scopus 로고
    • For reviews, see: a) D. Basavaiah, P. D. Rao, R. S. Hyma, Tetrahedron 1996, 52, 8001-8062; b) S. E. Drewes, G. H. P. Roo, Tetrahedron 1988, 44, 4653-4670; c) E. Ciganek, Org. React. 1997, 51, 201-350; d) P. Langer, Angew. Chem. Int. Ed. 2000, 39, 3049-3052; e) E. Ciganek, Org. React. 1997, 51, 201-350; f) D. Basavaiah, A. J. Rao, T. Satyanarayana, Chem. Rev. 2003, 103, 811-892.
    • (1997) Org. React. , vol.51 , pp. 201-350
    • Ciganek, E.1
  • 6
    • 0037366617 scopus 로고    scopus 로고
    • For reviews, see: a) D. Basavaiah, P. D. Rao, R. S. Hyma, Tetrahedron 1996, 52, 8001-8062; b) S. E. Drewes, G. H. P. Roo, Tetrahedron 1988, 44, 4653-4670; c) E. Ciganek, Org. React. 1997, 51, 201-350; d) P. Langer, Angew. Chem. Int. Ed. 2000, 39, 3049-3052; e) E. Ciganek, Org. React. 1997, 51, 201-350; f) D. Basavaiah, A. J. Rao, T. Satyanarayana, Chem. Rev. 2003, 103, 811-892.
    • (2003) Chem. Rev. , vol.103 , pp. 811-892
    • Basavaiah, D.1    Rao, A.J.2    Satyanarayana, T.3
  • 8
    • 4243830773 scopus 로고
    • Ger. Offen. 2,155,113, 1972
    • a) A. B. Baylis, M. E. D. Hillman, Ger. Offen. 2,155,113, 1972; Chem. Abstr. 1972, 77, 34174q; M. E. D. Hillman, A. B. Baylis, U. S. Patent 3,743,669, 1973;
    • (1972) Chem. Abstr. , vol.77
    • Baylis, A.B.1    Hillman, M.E.D.2
  • 9
    • 5144231021 scopus 로고    scopus 로고
    • U. S. Patent 3,743,669, 1973
    • a) A. B. Baylis, M. E. D. Hillman, Ger. Offen. 2,155,113, 1972; Chem. Abstr. 1972, 77, 34174q; M. E. D. Hillman, A. B. Baylis, U. S. Patent 3,743,669, 1973;
    • Hillman, M.E.D.1    Baylis, A.B.2
  • 12
    • 5144226919 scopus 로고
    • a) J. S. Hill, N. S. Isaacs, J. Chem. Res. (S) 1988, 330; J. Chem. Res. (M) 1988, 2641;
    • (1988) J. Chem. Res. (M) , pp. 2641
  • 20
    • 0035929305 scopus 로고    scopus 로고
    • Aza-Baylis-Hillman reaction: a) M. Shi, Y.-M. Xu, Chem. Commun. 2001, 1876-1877; b) M. Shi, Y.-M. Xu, Eur. J. Org. Chem. 2002, 696-701; c) M. Shi, Y.-M. Xu, G.-L. Zhao, X.-F. Wu, Eur. J. Org. Chem. 2002, 3666-3679; d) M. Shi, G.-L. Zhao, Tetrahedron Lett. 2002, 43, 4499-4502; e) M. Shi, Y.-M. Xu, J. Org. Chem. 2003, 68, 4784-4790; f) M. Shi, Y.-M. Xu, Angew. Chem. Int. Ed. 2002, 41, 4507-4510; g) M. Shi, L. H. Chen, Chem. Commun. 2003, 1310-1311; h) M. Shi, Y.-M. Xu, J. Org. Chem. 2004, 69, 417-425;
    • (2001) Chem. Commun. , pp. 1876-1877
    • Shi, M.1    Xu, Y.-M.2
  • 21
    • 0036180348 scopus 로고    scopus 로고
    • Aza-Baylis-Hillman reaction: a) M. Shi, Y.-M. Xu, Chem. Commun. 2001, 1876-1877; b) M. Shi, Y.-M. Xu, Eur. J. Org. Chem. 2002, 696-701; c) M. Shi, Y.-M. Xu, G.-L. Zhao, X.-F. Wu, Eur. J. Org. Chem. 2002, 3666-3679; d) M. Shi, G.-L. Zhao, Tetrahedron Lett. 2002, 43, 4499-4502; e) M. Shi, Y.-M. Xu, J. Org. Chem, 2003, 68, 4784-4790; f) M. Shi, Y.-M. Xu, Angew. Chem. Int. Ed. 2002, 41, 4507-4510; g) M. Shi, L. H. Chen, Chem. Commun. 2003, 1310-1311; h) M. Shi, Y.-M. Xu, J. Org. Chem. 2004, 69, 417-425;
    • (2002) Eur. J. Org. Chem. , pp. 696-701
    • Shi, M.1    Xu, Y.-M.2
  • 22
    • 0036846203 scopus 로고    scopus 로고
    • Aza-Baylis-Hillman reaction: a) M. Shi, Y.-M. Xu, Chem. Commun. 2001, 1876-1877; b) M. Shi, Y.-M. Xu, Eur. J. Org. Chem. 2002, 696-701; c) M. Shi, Y.-M. Xu, G.-L. Zhao, X.-F. Wu, Eur. J. Org. Chem. 2002, 3666-3679; d) M. Shi, G.-L. Zhao, Tetrahedron Lett. 2002, 43, 4499-4502; e) M. Shi, Y.-M. Xu, J. Org. Chem, 2003, 68, 4784-4790; f) M. Shi, Y.-M. Xu, Angew. Chem. Int. Ed. 2002, 41, 4507-4510; g) M. Shi, L. H. Chen, Chem. Commun. 2003, 1310-1311; h) M. Shi, Y.-M. Xu, J. Org. Chem. 2004, 69, 417-425;
    • (2002) Eur. J. Org. Chem. , pp. 3666-3679
    • Shi, M.1    Xu, Y.-M.2    Zhao, G.-L.3    Wu, X.-F.4
  • 23
    • 0037124397 scopus 로고    scopus 로고
    • Aza-Baylis-Hillman reaction: a) M. Shi, Y.-M. Xu, Chem. Commun. 2001, 1876-1877; b) M. Shi, Y.-M. Xu, Eur. J. Org. Chem. 2002, 696-701; c) M. Shi, Y.-M. Xu, G.-L. Zhao, X.-F. Wu, Eur. J. Org. Chem. 2002, 3666-3679; d) M. Shi, G.-L. Zhao, Tetrahedron Lett. 2002, 43, 4499-4502; e) M. Shi, Y.-M. Xu, J. Org. Chem, 2003, 68, 4784-4790; f) M. Shi, Y.-M. Xu, Angew. Chem. Int. Ed. 2002, 41, 4507-4510; g) M. Shi, L. H. Chen, Chem. Commun. 2003, 1310-1311; h) M. Shi, Y.-M. Xu, J. Org. Chem. 2004, 69, 417-425;
    • (2002) Tetrahedron Lett. , vol.43 , pp. 4499-4502
    • Shi, M.1    Zhao, G.-L.2
  • 24
    • 0038278402 scopus 로고    scopus 로고
    • Aza-Baylis-Hillman reaction: a) M. Shi, Y.-M. Xu, Chem. Commun. 2001, 1876-1877; b) M. Shi, Y.-M. Xu, Eur. J. Org. Chem. 2002, 696-701; c) M. Shi, Y.-M. Xu, G.-L. Zhao, X.-F. Wu, Eur. J. Org. Chem. 2002, 3666-3679; d) M. Shi, G.-L. Zhao, Tetrahedron Lett. 2002, 43, 4499-4502; e) M. Shi, Y.-M. Xu, J. Org. Chem, 2003, 68, 4784-4790; f) M. Shi, Y.-M. Xu, Angew. Chem. Int. Ed. 2002, 41, 4507-4510; g) M. Shi, L. H. Chen, Chem. Commun. 2003, 1310-1311; h) M. Shi, Y.-M. Xu, J. Org. Chem. 2004, 69, 417-425;
    • (2003) J. Org. Chem , vol.68 , pp. 4784-4790
    • Shi, M.1    Xu, Y.-M.2
  • 25
    • 0037011306 scopus 로고    scopus 로고
    • Aza-Baylis-Hillman reaction: a) M. Shi, Y.-M. Xu, Chem. Commun. 2001, 1876-1877; b) M. Shi, Y.-M. Xu, Eur. J. Org. Chem. 2002, 696-701; c) M. Shi, Y.-M. Xu, G.-L. Zhao, X.-F. Wu, Eur. J. Org. Chem. 2002, 3666-3679; d) M. Shi, G.-L. Zhao, Tetrahedron Lett. 2002, 43, 4499-4502; e) M. Shi, Y.-M. Xu, J. Org. Chem, 2003, 68, 4784-4790; f) M. Shi, Y.-M. Xu, Angew. Chem. Int. Ed. 2002, 41, 4507-4510; g) M. Shi, L. H. Chen, Chem. Commun. 2003, 1310-1311; h) M. Shi, Y.-M. Xu, J. Org. Chem. 2004, 69, 417-425;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4507-4510
    • Shi, M.1    Xu, Y.-M.2
  • 26
    • 0038696449 scopus 로고    scopus 로고
    • Aza-Baylis-Hillman reaction: a) M. Shi, Y.-M. Xu, Chem. Commun. 2001, 1876-1877; b) M. Shi, Y.-M. Xu, Eur. J. Org. Chem. 2002, 696-701; c) M. Shi, Y.-M. Xu, G.-L. Zhao, X.-F. Wu, Eur. J. Org. Chem. 2002, 3666-3679; d) M. Shi, G.-L. Zhao, Tetrahedron Lett. 2002, 43, 4499-4502; e) M. Shi, Y.-M. Xu, J. Org. Chem, 2003, 68, 4784-4790; f) M. Shi, Y.-M. Xu, Angew. Chem. Int. Ed. 2002, 41, 4507-4510; g) M. Shi, L. H. Chen, Chem. Commun. 2003, 1310-1311; h) M. Shi, Y.-M. Xu, J. Org. Chem. 2004, 69, 417-425;
    • (2003) Chem. Commun. , pp. 1310-1311
    • Shi, M.1    Chen, L.H.2
  • 27
    • 0347763335 scopus 로고    scopus 로고
    • Aza-Baylis-Hillman reaction: a) M. Shi, Y.-M. Xu, Chem. Commun. 2001, 1876-1877; b) M. Shi, Y.-M. Xu, Eur. J. Org. Chem. 2002, 696-701; c) M. Shi, Y.-M. Xu, G.-L. Zhao, X.-F. Wu, Eur. J. Org. Chem. 2002, 3666-3679; d) M. Shi, G.-L. Zhao, Tetrahedron Lett. 2002, 43, 4499-4502; e) M. Shi, Y.-M. Xu, J. Org. Chem, 2003, 68, 4784-4790; f) M. Shi, Y.-M. Xu, Angew. Chem. Int. Ed. 2002, 41, 4507-4510; g) M. Shi, L. H. Chen, Chem. Commun. 2003, 1310-1311; h) M. Shi, Y.-M. Xu, J. Org. Chem. 2004, 69, 417-425;
    • (2004) J. Org. Chem. , vol.69 , pp. 417-425
    • Shi, M.1    Xu, Y.-M.2
  • 28
    • 0000077082 scopus 로고
    • For previous reports related to the Baylis-Hillman reaction of methyl acrylate with imines, see: i) P. Perlmutter, C. C. Teo, Tetrahedron Lett. 1984, 25, 5951-5952; j) M. Takagi, K. Yamamoto, Tetrahedron 1991, 47, 8869-8882;
    • (1984) Tetrahedron Lett. , vol.25 , pp. 5951-5952
    • Perlmutter, P.1    Teo, C.C.2
  • 29
    • 0025991561 scopus 로고
    • For previous reports related to the Baylis-Hillman reaction of methyl acrylate with imines, see: i) P. Perlmutter, C. C. Teo, Tetrahedron Lett. 1984, 25, 5951-5952; j) M. Takagi, K. Yamamoto, Tetrahedron 1991, 47, 8869-8882;
    • (1991) Tetrahedron , vol.47 , pp. 8869-8882
    • Takagi, M.1    Yamamoto, K.2
  • 30
    • 0001266408 scopus 로고
    • for previous reports related to the Baylis-Hillman reaction of MVK with imine generated in situ, see: k) S. Bertenshow, M. Kahn, Tetrahedron Lett. 1989, 30, 2731-2732; l) D. Balan, H. Adolfsson, J. Org. Chem. 2002, 67, 2329-2334 and references cited therein.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 2731-2732
    • Bertenshow, S.1    Kahn, M.2
  • 31
    • 0037023405 scopus 로고    scopus 로고
    • and references cited therein
    • for previous reports related to the Baylis-Hillman reaction of MVK with imine generated in situ, see: k) S. Bertenshow, M. Kahn, Tetrahedron Lett. 1989, 30, 2731-2732; l) D. Balan, H. Adolfsson, J. Org. Chem. 2002, 67, 2329-2334 and references cited therein.
    • (2002) J. Org. Chem. , vol.67 , pp. 2329-2334
    • Balan, D.1    Adolfsson, H.2


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