메뉴 건너뛰기




Volumn , Issue 9, 2000, Pages 1815-1820

Enantioselective preparation of 2,4-disubstituted azetidines

Author keywords

Chiral azetidines; Palladacycles; Palladium catalysed couplings

Indexed keywords

AZETIDINE DERIVATIVE;

EID: 0034107428     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(200005)2000:9<1815::aid-ejoc1815>3.0.co;2-8     Document Type: Article
Times cited : (47)

References (62)
  • 1
    • 0028272321 scopus 로고
    • D. Tanner, P. G. Andersson, A. Harden, P. Somfai, Tetrahedron Lett. 1994, 35, 4631. P. G. Andersson, A. Harden, D. Tanner, P.-O. Norrby, Chem. Eur. J. 1995, 1, 12. P. G. Andersson, F. Johansson, D. Tanner, Tetrahedron 1998, 54, 11549. D. Tanner, F. Johansson, A. Harden, P. G. Andersson, Tetrahedron 1998, 54, 15731.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 4631
    • Tanner, D.1    Andersson, P.G.2    Harden, A.3    Somfai, P.4
  • 2
    • 84989591506 scopus 로고
    • D. Tanner, P. G. Andersson, A. Harden, P. Somfai, Tetrahedron Lett. 1994, 35, 4631. P. G. Andersson, A. Harden, D. Tanner, P.-O. Norrby, Chem. Eur. J. 1995, 1, 12. P. G. Andersson, F. Johansson, D. Tanner, Tetrahedron 1998, 54, 11549. D. Tanner, F. Johansson, A. Harden, P. G. Andersson, Tetrahedron 1998, 54, 15731.
    • (1995) Chem. Eur. J. , vol.1 , pp. 12
    • Andersson, P.G.1    Harden, A.2    Tanner, D.3    Norrby, P.-O.4
  • 3
    • 0032541549 scopus 로고    scopus 로고
    • D. Tanner, P. G. Andersson, A. Harden, P. Somfai, Tetrahedron Lett. 1994, 35, 4631. P. G. Andersson, A. Harden, D. Tanner, P.-O. Norrby, Chem. Eur. J. 1995, 1, 12. P. G. Andersson, F. Johansson, D. Tanner, Tetrahedron 1998, 54, 11549. D. Tanner, F. Johansson, A. Harden, P. G. Andersson, Tetrahedron 1998, 54, 15731.
    • (1998) Tetrahedron , vol.54 , pp. 11549
    • Andersson, P.G.1    Johansson, F.2    Tanner, D.3
  • 4
    • 0032542113 scopus 로고    scopus 로고
    • D. Tanner, P. G. Andersson, A. Harden, P. Somfai, Tetrahedron Lett. 1994, 35, 4631. P. G. Andersson, A. Harden, D. Tanner, P.-O. Norrby, Chem. Eur. J. 1995, 1, 12. P. G. Andersson, F. Johansson, D. Tanner, Tetrahedron 1998, 54, 11549. D. Tanner, F. Johansson, A. Harden, P. G. Andersson, Tetrahedron 1998, 54, 15731.
    • (1998) Tetrahedron , vol.54 , pp. 15731
    • Tanner, D.1    Johansson, F.2    Harden, A.3    Andersson, P.G.4
  • 6
    • 0037949403 scopus 로고
    • L. A. Van de Kuil, Y. S. J. Veldhuizen, D. M. Grove, J. W. Zwikker, L. W. Jenneskens, W. Drenth, W. J. J. Smeets, A. L. Spek, G. van Koten, Recl. Trav. Chim. Pays-Bas 1994, 113, 267. M. Shi, Y. Satoh, T. Makihara, Y. Masaki, Tetrahedron: Asymmetry 1995, 6, 2109. J. A. Sweet, J. M. Cavallari, W. A. Price, J. W. Ziller, D. V. McGrath, Tetrahedron: Asymmetry 1997, 8, 207. J. P. Cahill, F. M. Bohnen, R. Goddard, C. Krüger, P. J. Guiry, Tetrahedron: Asymmetry 1998, 9, 3831. J. P. Cahill, P. J. Guiry, Tetrahedron: Asymmetry 1998, 9, 4301. J. P. Cahill, A. P. Lightfoot, R. Goddard, J. Rust, P. J. Guiry, Tetrahedron: Asymmetry 1998, 9, 4307.
    • (1994) Recl. Trav. Chim. Pays-bas , vol.113 , pp. 267
    • Van De Kuil, L.A.1    Veldhuizen, Y.S.J.2    Grove, D.M.3    Zwikker, J.W.4    Jenneskens, L.W.5    Drenth, W.6    Smeets, W.J.J.7    Spek, A.L.8    Van Koten, G.9
  • 7
    • 0029143575 scopus 로고
    • L. A. Van de Kuil, Y. S. J. Veldhuizen, D. M. Grove, J. W. Zwikker, L. W. Jenneskens, W. Drenth, W. J. J. Smeets, A. L. Spek, G. van Koten, Recl. Trav. Chim. Pays-Bas 1994, 113, 267. M. Shi, Y. Satoh, T. Makihara, Y. Masaki, Tetrahedron: Asymmetry 1995, 6, 2109. J. A. Sweet, J. M. Cavallari, W. A. Price, J. W. Ziller, D. V. McGrath, Tetrahedron: Asymmetry 1997, 8, 207. J. P. Cahill, F. M. Bohnen, R. Goddard, C. Krüger, P. J. Guiry, Tetrahedron: Asymmetry 1998, 9, 3831. J. P. Cahill, P. J. Guiry, Tetrahedron: Asymmetry 1998, 9, 4301. J. P. Cahill, A. P. Lightfoot, R. Goddard, J. Rust, P. J. Guiry, Tetrahedron: Asymmetry 1998, 9, 4307.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 2109
    • Shi, M.1    Satoh, Y.2    Makihara, T.3    Masaki, Y.4
  • 8
    • 0031036227 scopus 로고    scopus 로고
    • L. A. Van de Kuil, Y. S. J. Veldhuizen, D. M. Grove, J. W. Zwikker, L. W. Jenneskens, W. Drenth, W. J. J. Smeets, A. L. Spek, G. van Koten, Recl. Trav. Chim. Pays-Bas 1994, 113, 267. M. Shi, Y. Satoh, T. Makihara, Y. Masaki, Tetrahedron: Asymmetry 1995, 6, 2109. J. A. Sweet, J. M. Cavallari, W. A. Price, J. W. Ziller, D. V. McGrath, Tetrahedron: Asymmetry 1997, 8, 207. J. P. Cahill, F. M. Bohnen, R. Goddard, C. Krüger, P. J. Guiry, Tetrahedron: Asymmetry 1998, 9, 3831. J. P. Cahill, P. J. Guiry, Tetrahedron: Asymmetry 1998, 9, 4301. J. P. Cahill, A. P. Lightfoot, R. Goddard, J. Rust, P. J. Guiry, Tetrahedron: Asymmetry 1998, 9, 4307.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 207
    • Sweet, J.A.1    Cavallari, J.M.2    Price, W.A.3    Ziller, J.W.4    McGrath, D.V.5
  • 9
    • 0032491618 scopus 로고    scopus 로고
    • L. A. Van de Kuil, Y. S. J. Veldhuizen, D. M. Grove, J. W. Zwikker, L. W. Jenneskens, W. Drenth, W. J. J. Smeets, A. L. Spek, G. van Koten, Recl. Trav. Chim. Pays-Bas 1994, 113, 267. M. Shi, Y. Satoh, T. Makihara, Y. Masaki, Tetrahedron: Asymmetry 1995, 6, 2109. J. A. Sweet, J. M. Cavallari, W. A. Price, J. W. Ziller, D. V. McGrath, Tetrahedron: Asymmetry 1997, 8, 207. J. P. Cahill, F. M. Bohnen, R. Goddard, C. Krüger, P. J. Guiry, Tetrahedron: Asymmetry 1998, 9, 3831. J. P. Cahill, P. J. Guiry, Tetrahedron: Asymmetry 1998, 9, 4301. J. P. Cahill, A. P. Lightfoot, R. Goddard, J. Rust, P. J. Guiry, Tetrahedron: Asymmetry 1998, 9, 4307.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 3831
    • Cahill, J.P.1    Bohnen, F.M.2    Goddard, R.3    Krüger, C.4    Guiry, P.J.5
  • 10
    • 0032564706 scopus 로고    scopus 로고
    • L. A. Van de Kuil, Y. S. J. Veldhuizen, D. M. Grove, J. W. Zwikker, L. W. Jenneskens, W. Drenth, W. J. J. Smeets, A. L. Spek, G. van Koten, Recl. Trav. Chim. Pays-Bas 1994, 113, 267. M. Shi, Y. Satoh, T. Makihara, Y. Masaki, Tetrahedron: Asymmetry 1995, 6, 2109. J. A. Sweet, J. M. Cavallari, W. A. Price, J. W. Ziller, D. V. McGrath, Tetrahedron: Asymmetry 1997, 8, 207. J. P. Cahill, F. M. Bohnen, R. Goddard, C. Krüger, P. J. Guiry, Tetrahedron: Asymmetry 1998, 9, 3831. J. P. Cahill, P. J. Guiry, Tetrahedron: Asymmetry 1998, 9, 4301. J. P. Cahill, A. P. Lightfoot, R. Goddard, J. Rust, P. J. Guiry, Tetrahedron: Asymmetry 1998, 9, 4307.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 4301
    • Cahill, J.P.1    Guiry, P.J.2
  • 11
    • 0032564687 scopus 로고    scopus 로고
    • L. A. Van de Kuil, Y. S. J. Veldhuizen, D. M. Grove, J. W. Zwikker, L. W. Jenneskens, W. Drenth, W. J. J. Smeets, A. L. Spek, G. van Koten, Recl. Trav. Chim. Pays-Bas 1994, 113, 267. M. Shi, Y. Satoh, T. Makihara, Y. Masaki, Tetrahedron: Asymmetry 1995, 6, 2109. J. A. Sweet, J. M. Cavallari, W. A. Price, J. W. Ziller, D. V. McGrath, Tetrahedron: Asymmetry 1997, 8, 207. J. P. Cahill, F. M. Bohnen, R. Goddard, C. Krüger, P. J. Guiry, Tetrahedron: Asymmetry 1998, 9, 3831. J. P. Cahill, P. J. Guiry, Tetrahedron: Asymmetry 1998, 9, 4301. J. P. Cahill, A. P. Lightfoot, R. Goddard, J. Rust, P. J. Guiry, Tetrahedron: Asymmetry 1998, 9, 4307.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 4307
    • Cahill, J.P.1    Lightfoot, A.P.2    Goddard, R.3    Rust, J.4    Guiry, P.J.5
  • 12
    • 0002032726 scopus 로고
    • For selected recent references, see: J. K. Whitesell, Chem. Rev. 1989, 89, 1581. J. K. Whitesell, S. W. Felman, J. Org. Chem. 1977, 42, 1663. J.-E. Bäckvall, C. Löfström, M. Maffei, V. Langer, Tetrahedron Lett. 1992, 33, 2417. V. S. M. Dankwardt, J. W. Dankwardt, R. H. Schlessinger, Tetrahedron Lett. 1998, 39, 4971. T. J. Donohoe, M. Helliwell, C. A. Stevenson, T. Ladduwahetty, Tetrahedron Lett. 1998, 39, 3071. J. M. Chong, I. S. Clarke, I. Koch, P. C. Olbach, N. J. Taylor, Tetrahedron: Asymmetry 1995, 6, 409 and references therein.
    • (1989) Chem. Rev. , vol.89 , pp. 1581
    • Whitesell, J.K.1
  • 13
    • 0001269461 scopus 로고
    • For selected recent references, see: J. K. Whitesell, Chem. Rev. 1989, 89, 1581. J. K. Whitesell, S. W. Felman, J. Org. Chem. 1977, 42, 1663. J.-E. Bäckvall, C. Löfström, M. Maffei, V. Langer, Tetrahedron Lett. 1992, 33, 2417. V. S. M. Dankwardt, J. W. Dankwardt, R. H. Schlessinger, Tetrahedron Lett. 1998, 39, 4971. T. J. Donohoe, M. Helliwell, C. A. Stevenson, T. Ladduwahetty, Tetrahedron Lett. 1998, 39, 3071. J. M. Chong, I. S. Clarke, I. Koch, P. C. Olbach, N. J. Taylor, Tetrahedron: Asymmetry 1995, 6, 409 and references therein.
    • (1977) J. Org. Chem. , vol.42 , pp. 1663
    • Whitesell, J.K.1    Felman, S.W.2
  • 14
    • 0026559061 scopus 로고
    • For selected recent references, see: J. K. Whitesell, Chem. Rev. 1989, 89, 1581. J. K. Whitesell, S. W. Felman, J. Org. Chem. 1977, 42, 1663. J.-E. Bäckvall, C. Löfström, M. Maffei, V. Langer, Tetrahedron Lett. 1992, 33, 2417. V. S. M. Dankwardt, J. W. Dankwardt, R. H. Schlessinger, Tetrahedron Lett. 1998, 39, 4971. T. J. Donohoe, M. Helliwell, C. A. Stevenson, T. Ladduwahetty, Tetrahedron Lett. 1998, 39, 3071. J. M. Chong, I. S. Clarke, I. Koch, P. C. Olbach, N. J. Taylor, Tetrahedron: Asymmetry 1995, 6, 409 and references therein.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 2417
    • Bäckvall, J.-E.1    Löfström, C.2    Maffei, M.3    Langer, V.4
  • 15
    • 0032499982 scopus 로고    scopus 로고
    • For selected recent references, see: J. K. Whitesell, Chem. Rev. 1989, 89, 1581. J. K. Whitesell, S. W. Felman, J. Org. Chem. 1977, 42, 1663. J.-E. Bäckvall, C. Löfström, M. Maffei, V. Langer, Tetrahedron Lett. 1992, 33, 2417. V. S. M. Dankwardt, J. W. Dankwardt, R. H. Schlessinger, Tetrahedron Lett. 1998, 39, 4971. T. J. Donohoe, M. Helliwell, C. A. Stevenson, T. Ladduwahetty, Tetrahedron Lett. 1998, 39, 3071. J. M. Chong, I. S. Clarke, I. Koch, P. C. Olbach, N. J. Taylor, Tetrahedron: Asymmetry 1995, 6, 409 and references therein.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 4971
    • Dankwardt, V.S.M.1    Dankwardt, J.W.2    Schlessinger, R.H.3
  • 16
    • 0032492983 scopus 로고    scopus 로고
    • For selected recent references, see: J. K. Whitesell, Chem. Rev. 1989, 89, 1581. J. K. Whitesell, S. W. Felman, J. Org. Chem. 1977, 42, 1663. J.-E. Bäckvall, C. Löfström, M. Maffei, V. Langer, Tetrahedron Lett. 1992, 33, 2417. V. S. M. Dankwardt, J. W. Dankwardt, R. H. Schlessinger, Tetrahedron Lett. 1998, 39, 4971. T. J. Donohoe, M. Helliwell, C. A. Stevenson, T. Ladduwahetty, Tetrahedron Lett. 1998, 39, 3071. J. M. Chong, I. S. Clarke, I. Koch, P. C. Olbach, N. J. Taylor, Tetrahedron: Asymmetry 1995, 6, 409 and references therein.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3071
    • Donohoe, T.J.1    Helliwell, M.2    Stevenson, C.A.3    Ladduwahetty, T.4
  • 17
    • 0028926606 scopus 로고
    • and references therein
    • For selected recent references, see: J. K. Whitesell, Chem. Rev. 1989, 89, 1581. J. K. Whitesell, S. W. Felman, J. Org. Chem. 1977, 42, 1663. J.-E. Bäckvall, C. Löfström, M. Maffei, V. Langer, Tetrahedron Lett. 1992, 33, 2417. V. S. M. Dankwardt, J. W. Dankwardt, R. H. Schlessinger, Tetrahedron Lett. 1998, 39, 4971. T. J. Donohoe, M. Helliwell, C. A. Stevenson, T. Ladduwahetty, Tetrahedron Lett. 1998, 39, 3071. J. M. Chong, I. S. Clarke, I. Koch, P. C. Olbach, N. J. Taylor, Tetrahedron: Asymmetry 1995, 6, 409 and references therein.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 409
    • Chong, J.M.1    Clarke, I.S.2    Koch, I.3    Olbach, P.C.4    Taylor, N.J.5
  • 21
    • 0026704156 scopus 로고
    • Selected examples: A. V. R. Rao, M. K. Gurjar, V. Kaiwar, Tetrahedron: Asymmetry 1992, 3, 859. W. A. J. Starmans, R. W. A. Walgers, L. Thijs, R. de Gelder, J. M. M. Smits, B. Zwanenburg, Tetrahedron 1998, 54, 4991.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 859
    • Rao, A.V.R.1    Gurjar, M.K.2    Kaiwar, V.3
  • 26
    • 0000913103 scopus 로고
    • I. Ojima, M. Zhao, T. Yamato, K. Nakahashi, J. Org. Chem. 1991, 56, 5263. G. V. Shustov, A. Rauk, J. Am. Chem. Soc. 1995, 117, 928. J. K. Lynch, M. W. Holladay, K. B. Ryther, H. Bai, C.-N. Hsiao, H. E. Morton, D. A. Dickman. W. Arnold, S. A. King, Tetrahedron: Asymmetry 1998, 9, 2791.
    • (1991) J. Org. Chem. , vol.56 , pp. 5263
    • Ojima, I.1    Zhao, M.2    Yamato, T.3    Nakahashi, K.4
  • 27
    • 0028861034 scopus 로고
    • I. Ojima, M. Zhao, T. Yamato, K. Nakahashi, J. Org. Chem. 1991, 56, 5263. G. V. Shustov, A. Rauk, J. Am. Chem. Soc. 1995, 117, 928. J. K. Lynch, M. W. Holladay, K. B. Ryther, H. Bai, C.-N. Hsiao, H. E. Morton, D. A. Dickman. W. Arnold, S. A. King, Tetrahedron: Asymmetry 1998, 9, 2791.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 928
    • Shustov, G.V.1    Rauk, A.2
  • 29
    • 0033548381 scopus 로고    scopus 로고
    • The synthesis of racemic 2,4-diphenylazetidines from anti-1,3-diphenyl-1,3-propanediol has recently been mentioned: G. H. P. Roos, A. R. Donovan, Tetrahedron: Asymmetry 1999, 10, 991.
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 991
    • Roos, G.H.P.1    Donovan, A.R.2
  • 31
    • 0032928212 scopus 로고    scopus 로고
    • and references therein
    • M. Kitamura, T. Ohkuma, S. Inoue, N. Sayo, H. Kumobayashi, S. Akutagawa, T. Ohta, H. Takaya, R. Noyori, J. Am. Chem. Soc. 1988, 11, 629. D. Blanc, V. Ratovelomanana-Vidal, A. Marinetti, J.-P. Genêt, Synlett 1999, 4, 480 and references therein.
    • (1999) Synlett , vol.4 , pp. 480
    • Blanc, D.1    Ratovelomanana-Vidal, V.2    Marinetti, A.3    Genêt, J.-P.4
  • 34
  • 35
    • 85088333762 scopus 로고    scopus 로고
    • note
    • AB = 12.6 Hz), respectively.
  • 37
    • 84943375045 scopus 로고
    • (Ed.: W. Lwowski), Pergamon, Oxford, and references therein
    • D. E. Davies, R. C. Starr, in: Comprehensive Heterocyclic Chemistry (Ed.: W. Lwowski), Pergamon, Oxford, 1984, vol. 7, part 5, p. 237 and references therein.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.7 , Issue.PART 5 , pp. 237
    • Davies, D.E.1    Starr, R.C.2
  • 39
    • 0000551863 scopus 로고
    • E. Juaristi, J. D. Reyna, Tetrahedron Lett. 1984, 25, 3521. E. Juaristi, D. Madrigal, Tetrahedron 1989, 45, 629.
    • (1989) Tetrahedron , vol.45 , pp. 629
    • Juaristi, E.1    Madrigal, D.2
  • 40
    • 0000441894 scopus 로고    scopus 로고
    • For recent reviews, see: J. F. Hartwig, Angew. Chem. Int. Ed. 1998, 37, 2047. J. P. Wolfe, S. Wagaw, J.-F. Marcoux, S. L. Buchwald, Acc. Chem. Res. 1998, 31, 805.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 2047
    • Hartwig, J.F.1
  • 54
    • 0030783848 scopus 로고    scopus 로고
    • T. K. Hollis, L. E. Overman, Tetrahedron Lett. 1997, 38, 8837. F. Cohen, L. E. Overman, Tetrahedron: Asymmetry 1998, 9, 3213. Y. Donde, L. E. Overman, J. Am. Chem. Soc. 1999, 121, 2933.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 8837
    • Hollis, T.K.1    Overman, L.E.2
  • 55
    • 0032544783 scopus 로고    scopus 로고
    • T. K. Hollis, L. E. Overman, Tetrahedron Lett. 1997, 38, 8837. F. Cohen, L. E. Overman, Tetrahedron: Asymmetry 1998, 9, 3213. Y. Donde, L. E. Overman, J. Am. Chem. Soc. 1999, 121, 2933.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 3213
    • Cohen, F.1    Overman, L.E.2
  • 56
    • 0033620464 scopus 로고    scopus 로고
    • T. K. Hollis, L. E. Overman, Tetrahedron Lett. 1997, 38, 8837. F. Cohen, L. E. Overman, Tetrahedron: Asymmetry 1998, 9, 3213. Y. Donde, L. E. Overman, J. Am. Chem. Soc. 1999, 121, 2933.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 2933
    • Donde, Y.1    Overman, L.E.2
  • 57
    • 0342695879 scopus 로고    scopus 로고
    • Commercially available from Aldrich Chemical Company
    • Commercially available from Aldrich Chemical Company.
  • 60
    • 0343130246 scopus 로고    scopus 로고
    • note
    • Assignments were made by treating 8 with (R)- and (S)-Binap in separate experiments.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.