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Volumn 37, Issue 18, 1998, Pages 2515-2517

A facile generation of a cyclopropylzinc compound from an alkenylzinc derivative and its reaction with electrophiles

Author keywords

Alkynes; Carbenoids; Copper; Cyclopropane; Zinc; Zirconium

Indexed keywords


EID: 0032476098     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981002)37:18<2515::AID-ANIE2515>3.0.CO;2-D     Document Type: Article
Times cited : (14)

References (37)
  • 1
    • 0004174399 scopus 로고
    • Academic Press, London
    • B. J. Wakefield, Organolithium Method, Academic Press, London, 1988; B. J. Wakefield, Organomagnesium Methods in Organic Synthesis, Academic Press, London, 1995.
    • (1988) Organolithium Method
    • Wakefield, B.J.1
  • 3
    • 0000718165 scopus 로고
    • For the preparation of cyclopropylmetal compounds by carbometalation of cyclopropene, see A. T. Stoll, E. Negishi, Tetrahedron Lett. 1985, 26, 5671-5674; E. Nakamura, M. Isaka, S. Matsuzawa, J. Am. Chem. Soc. 1988, 110, 1297-1298; M. Isaka, E. Nakamura, J. Am. Chem. Soc. 1990, 112, 7428-7430; K. Kubota, M. Nakamura, E. Nakamura, J. Am. Chem. Soc. 1993, 115, 5867-5868; M. Nakamura, M. Arai, E. Nakamura, J. Am. Chem. Soc. 1995, 117, 1179-1180; E. Nakamura, Pure Appl. Chem. 1996, 68, 123-130.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 5671-5674
    • Stoll, A.T.1    Negishi, E.2
  • 4
    • 33845278707 scopus 로고
    • For the preparation of cyclopropylmetal compounds by carbometalation of cyclopropene, see A. T. Stoll, E. Negishi, Tetrahedron Lett. 1985, 26, 5671-5674; E. Nakamura, M. Isaka, S. Matsuzawa, J. Am. Chem. Soc. 1988, 110, 1297-1298; M. Isaka, E. Nakamura, J. Am. Chem. Soc. 1990, 112, 7428-7430; K. Kubota, M. Nakamura, E. Nakamura, J. Am. Chem. Soc. 1993, 115, 5867-5868; M. Nakamura, M. Arai, E. Nakamura, J. Am. Chem. Soc. 1995, 117, 1179-1180; E. Nakamura, Pure Appl. Chem. 1996, 68, 123-130.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 1297-1298
    • Nakamura, E.1    Isaka, M.2    Matsuzawa, S.3
  • 5
    • 0001643620 scopus 로고
    • For the preparation of cyclopropylmetal compounds by carbometalation of cyclopropene, see A. T. Stoll, E. Negishi, Tetrahedron Lett. 1985, 26, 5671-5674; E. Nakamura, M. Isaka, S. Matsuzawa, J. Am. Chem. Soc. 1988, 110, 1297-1298; M. Isaka, E. Nakamura, J. Am. Chem. Soc. 1990, 112, 7428-7430; K. Kubota, M. Nakamura, E. Nakamura, J. Am. Chem. Soc. 1993, 115, 5867-5868; M. Nakamura, M. Arai, E. Nakamura, J. Am. Chem. Soc. 1995, 117, 1179-1180; E. Nakamura, Pure Appl. Chem. 1996, 68, 123-130.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 7428-7430
    • Isaka, M.1    Nakamura, E.2
  • 6
    • 0001381256 scopus 로고
    • For the preparation of cyclopropylmetal compounds by carbometalation of cyclopropene, see A. T. Stoll, E. Negishi, Tetrahedron Lett. 1985, 26, 5671-5674; E. Nakamura, M. Isaka, S. Matsuzawa, J. Am. Chem. Soc. 1988, 110, 1297-1298; M. Isaka, E. Nakamura, J. Am. Chem. Soc. 1990, 112, 7428-7430; K. Kubota, M. Nakamura, E. Nakamura, J. Am. Chem. Soc. 1993, 115, 5867-5868; M. Nakamura, M. Arai, E. Nakamura, J. Am. Chem. Soc. 1995, 117, 1179-1180; E. Nakamura, Pure Appl. Chem. 1996, 68, 123-130.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 5867-5868
    • Kubota, K.1    Nakamura, M.2    Nakamura, E.3
  • 7
    • 0000547863 scopus 로고
    • For the preparation of cyclopropylmetal compounds by carbometalation of cyclopropene, see A. T. Stoll, E. Negishi, Tetrahedron Lett. 1985, 26, 5671-5674; E. Nakamura, M. Isaka, S. Matsuzawa, J. Am. Chem. Soc. 1988, 110, 1297-1298; M. Isaka, E. Nakamura, J. Am. Chem. Soc. 1990, 112, 7428-7430; K. Kubota, M. Nakamura, E. Nakamura, J. Am. Chem. Soc. 1993, 115, 5867-5868; M. Nakamura, M. Arai, E. Nakamura, J. Am. Chem. Soc. 1995, 117, 1179-1180; E. Nakamura, Pure Appl. Chem. 1996, 68, 123-130.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 1179-1180
    • Nakamura, M.1    Arai, M.2    Nakamura, E.3
  • 8
    • 0000945222 scopus 로고    scopus 로고
    • For the preparation of cyclopropylmetal compounds by carbometalation of cyclopropene, see A. T. Stoll, E. Negishi, Tetrahedron Lett. 1985, 26, 5671-5674; E. Nakamura, M. Isaka, S. Matsuzawa, J. Am. Chem. Soc. 1988, 110, 1297-1298; M. Isaka, E. Nakamura, J. Am. Chem. Soc. 1990, 112, 7428-7430; K. Kubota, M. Nakamura, E. Nakamura, J. Am. Chem. Soc. 1993, 115, 5867-5868; M. Nakamura, M. Arai, E. Nakamura, J. Am. Chem. Soc. 1995, 117, 1179-1180; E. Nakamura, Pure Appl. Chem. 1996, 68, 123-130.
    • (1996) Pure Appl. Chem. , vol.68 , pp. 123-130
    • Nakamura, E.1
  • 10
    • 0011795338 scopus 로고
    • J. R. A. Dulayymi, M. S. Baird, I. G. Bolesov, V. Tveresovsky, M. Rubin, Tetrahedron Lett. 1996, 37, 8933-8936; J. T. Groves, K. W. Ma, J. Am. Chem. Soc. 1974, 96, 6527-6529; C. W. Jefford, D. Kirkpatrick, F. Delay, J. Am. Chem. Soc. 1972, 94, 8905-8907.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 6527-6529
    • Groves, J.T.1    Ma, K.W.2
  • 11
    • 0010787852 scopus 로고
    • J. R. A. Dulayymi, M. S. Baird, I. G. Bolesov, V. Tveresovsky, M. Rubin, Tetrahedron Lett. 1996, 37, 8933-8936; J. T. Groves, K. W. Ma, J. Am. Chem. Soc. 1974, 96, 6527-6529; C. W. Jefford, D. Kirkpatrick, F. Delay, J. Am. Chem. Soc. 1972, 94, 8905-8907.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 8905-8907
    • Jefford, C.W.1    Kirkpatrick, D.2    Delay, F.3
  • 12
    • 33751553350 scopus 로고
    • Boron: a) T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986-4988; b) P. Fontani, B. Carboni, M. Vaultier, G. Maas, Synthesis 1991, 605-609; c) X.-Z. Wang, M.-Z. Deng, J. Chem. Soc. Perkin. Trans. 1 1996, 2663-2664; d) J. P. Hildebrand, S. P. Marsden, Synlett 1996, 893-894; e) J. Pietruszka, M. Widenmeyer, Synlett 1997, 977-979; f) J. E. A. Luithle, J. Pietruszka, Liebigs Ann. 1997, 2297-2302; aluminum: G. Zweifel, G. M. Clark, C. C. Whitney, J. Am. Chem. Soc. 1971, 93, 1305-1307; silicon: K. Hirabayashi, A. Mori, T. Hiyama, Tetrahedron Lett. 1997, 38, 461-464; tin: D. Seyferth, H. M. Cohen, Inorg. Chem. 1961, 1, 913-916.
    • (1990) J. Org. Chem. , vol.55 , pp. 4986-4988
    • Imai, T.1    Mineta, H.2    Nishida, S.3
  • 13
    • 0025824041 scopus 로고
    • Boron: a) T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986-4988; b) P. Fontani, B. Carboni, M. Vaultier, G. Maas, Synthesis 1991, 605-609; c) X.-Z. Wang, M.-Z. Deng, J. Chem. Soc. Perkin. Trans. 1 1996, 2663-2664; d) J. P. Hildebrand, S. P. Marsden, Synlett 1996, 893-894; e) J. Pietruszka, M. Widenmeyer, Synlett 1997, 977-979; f) J. E. A. Luithle, J. Pietruszka, Liebigs Ann. 1997, 2297-2302; aluminum: G. Zweifel, G. M. Clark, C. C. Whitney, J. Am. Chem. Soc. 1971, 93, 1305-1307; silicon: K. Hirabayashi, A. Mori, T. Hiyama, Tetrahedron Lett. 1997, 38, 461-464; tin: D. Seyferth, H. M. Cohen, Inorg. Chem. 1961, 1, 913-916.
    • (1991) Synthesis , pp. 605-609
    • Fontani, P.1    Carboni, B.2    Vaultier, M.3    Maas, G.4
  • 14
    • 0001549365 scopus 로고    scopus 로고
    • Boron: a) T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986-4988; b) P. Fontani, B. Carboni, M. Vaultier, G. Maas, Synthesis 1991, 605-609; c) X.-Z. Wang, M.-Z. Deng, J. Chem. Soc. Perkin. Trans. 1 1996, 2663-2664; d) J. P. Hildebrand, S. P. Marsden, Synlett 1996, 893-894; e) J. Pietruszka, M. Widenmeyer, Synlett 1997, 977-979; f) J. E. A. Luithle, J. Pietruszka, Liebigs Ann. 1997, 2297-2302; aluminum: G. Zweifel, G. M. Clark, C. C. Whitney, J. Am. Chem. Soc. 1971, 93, 1305-1307; silicon: K. Hirabayashi, A. Mori, T. Hiyama, Tetrahedron Lett. 1997, 38, 461-464; tin: D. Seyferth, H. M. Cohen, Inorg. Chem. 1961, 1, 913-916.
    • (1996) J. Chem. Soc. Perkin. Trans. 1 , pp. 2663-2664
    • Wang, X.-Z.1    Deng, M.-Z.2
  • 15
    • 0342538255 scopus 로고    scopus 로고
    • Boron: a) T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986-4988; b) P. Fontani, B. Carboni, M. Vaultier, G. Maas, Synthesis 1991, 605-609; c) X.-Z. Wang, M.-Z. Deng, J. Chem. Soc. Perkin. Trans. 1 1996, 2663-2664; d) J. P. Hildebrand, S. P. Marsden, Synlett 1996, 893-894; e) J. Pietruszka, M. Widenmeyer, Synlett 1997, 977-979; f) J. E. A. Luithle, J. Pietruszka, Liebigs Ann. 1997, 2297-2302; aluminum: G. Zweifel, G. M. Clark, C. C. Whitney, J. Am. Chem. Soc. 1971, 93, 1305-1307; silicon: K. Hirabayashi, A. Mori, T. Hiyama, Tetrahedron Lett. 1997, 38, 461-464; tin: D. Seyferth, H. M. Cohen, Inorg. Chem. 1961, 1, 913-916.
    • (1996) Synlett , pp. 893-894
    • Hildebrand, J.P.1    Marsden, S.P.2
  • 16
    • 0002803025 scopus 로고    scopus 로고
    • Boron: a) T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986-4988; b) P. Fontani, B. Carboni, M. Vaultier, G. Maas, Synthesis 1991, 605-609; c) X.-Z. Wang, M.-Z. Deng, J. Chem. Soc. Perkin. Trans. 1 1996, 2663-2664; d) J. P. Hildebrand, S. P. Marsden, Synlett 1996, 893-894; e) J. Pietruszka, M. Widenmeyer, Synlett 1997, 977-979; f) J. E. A. Luithle, J. Pietruszka, Liebigs Ann. 1997, 2297-2302; aluminum: G. Zweifel, G. M. Clark, C. C. Whitney, J. Am. Chem. Soc. 1971, 93, 1305-1307; silicon: K. Hirabayashi, A. Mori, T. Hiyama, Tetrahedron Lett. 1997, 38, 461-464; tin: D. Seyferth, H. M. Cohen, Inorg. Chem. 1961, 1, 913-916.
    • (1997) Synlett , pp. 977-979
    • Pietruszka, J.1    Widenmeyer, M.2
  • 17
    • 0006319534 scopus 로고    scopus 로고
    • Boron: a) T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986-4988; b) P. Fontani, B. Carboni, M. Vaultier, G. Maas, Synthesis 1991, 605-609; c) X.-Z. Wang, M.-Z. Deng, J. Chem. Soc. Perkin. Trans. 1 1996, 2663-2664; d) J. P. Hildebrand, S. P. Marsden, Synlett 1996, 893-894; e) J. Pietruszka, M. Widenmeyer, Synlett 1997, 977-979; f) J. E. A. Luithle, J. Pietruszka, Liebigs Ann. 1997, 2297-2302; aluminum: G. Zweifel, G. M. Clark, C. C. Whitney, J. Am. Chem. Soc. 1971, 93, 1305-1307; silicon: K. Hirabayashi, A. Mori, T. Hiyama, Tetrahedron Lett. 1997, 38, 461-464; tin: D. Seyferth, H. M. Cohen, Inorg. Chem. 1961, 1, 913-916.
    • (1997) Liebigs Ann. , pp. 2297-2302
    • Luithle, J.E.A.1    Pietruszka, J.2
  • 18
    • 0008480094 scopus 로고
    • Boron: a) T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986-4988; b) P. Fontani, B. Carboni, M. Vaultier, G. Maas, Synthesis 1991, 605-609; c) X.-Z. Wang, M.-Z. Deng, J. Chem. Soc. Perkin. Trans. 1 1996, 2663-2664; d) J. P. Hildebrand, S. P. Marsden, Synlett 1996, 893-894; e) J. Pietruszka, M. Widenmeyer, Synlett 1997, 977-979; f) J. E. A. Luithle, J. Pietruszka, Liebigs Ann. 1997, 2297-2302; aluminum: G. Zweifel, G. M. Clark, C. C. Whitney, J. Am. Chem. Soc. 1971, 93, 1305-1307; silicon: K. Hirabayashi, A. Mori, T. Hiyama, Tetrahedron Lett. 1997, 38, 461-464; tin: D. Seyferth, H. M. Cohen, Inorg. Chem. 1961, 1, 913-916.
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 1305-1307
    • Zweifel, G.1    Clark, G.M.2    Whitney, C.C.3
  • 19
    • 0031023977 scopus 로고    scopus 로고
    • Boron: a) T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986-4988; b) P. Fontani, B. Carboni, M. Vaultier, G. Maas, Synthesis 1991, 605-609; c) X.-Z. Wang, M.-Z. Deng, J. Chem. Soc. Perkin. Trans. 1 1996, 2663-2664; d) J. P. Hildebrand, S. P. Marsden, Synlett 1996, 893-894; e) J. Pietruszka, M. Widenmeyer, Synlett 1997, 977-979; f) J. E. A. Luithle, J. Pietruszka, Liebigs Ann. 1997, 2297-2302; aluminum: G. Zweifel, G. M. Clark, C. C. Whitney, J. Am. Chem. Soc. 1971, 93, 1305-1307; silicon: K. Hirabayashi, A. Mori, T. Hiyama, Tetrahedron Lett. 1997, 38, 461-464; tin: D. Seyferth, H. M. Cohen, Inorg. Chem. 1961, 1, 913-916.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 461-464
    • Hirabayashi, K.1    Mori, A.2    Hiyama, T.3
  • 20
    • 0000509961 scopus 로고
    • Boron: a) T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986-4988; b) P. Fontani, B. Carboni, M. Vaultier, G. Maas, Synthesis 1991, 605-609; c) X.-Z. Wang, M.-Z. Deng, J. Chem. Soc. Perkin. Trans. 1 1996, 2663-2664; d) J. P. Hildebrand, S. P. Marsden, Synlett 1996, 893-894; e) J. Pietruszka, M. Widenmeyer, Synlett 1997, 977-979; f) J. E. A. Luithle, J. Pietruszka, Liebigs Ann. 1997, 2297-2302; aluminum: G. Zweifel, G. M. Clark, C. C. Whitney, J. Am. Chem. Soc. 1971, 93, 1305-1307; silicon: K. Hirabayashi, A. Mori, T. Hiyama, Tetrahedron Lett. 1997, 38, 461-464; tin: D. Seyferth, H. M. Cohen, Inorg. Chem. 1961, 1, 913-916.
    • (1961) Inorg. Chem. , vol.1 , pp. 913-916
    • Seyferth, D.1    Cohen, H.M.2
  • 23
    • 0344015394 scopus 로고    scopus 로고
    • note
    • 2 in the place of iPrZnCl afforded (E)-4 in 37% yield.
  • 26
    • 0026630314 scopus 로고
    • A. Sidduri, M. J. Rozema, P. Knochel, J. Org. Chem. 1993, 58, 2694-2713; A. Sidduri, P. Knochel, J. Am. Chem. Soc. 1992, 114, 7579-7581.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 7579-7581
    • Sidduri, A.1    Knochel, P.2
  • 27
    • 33845280673 scopus 로고
    • P. Knochel, M. C. P. Yeh, S. C. Berk, J. Talbert, J. Org. Chem. 1988, 53, 2390-2392; L. Micouin, P. Knochel, Synlett 1997, 327-328; P. Knochel, R. D. Singer, Chem. Rev. 1993, 93, 2117-2188; P. Knochel, Synlett 1995, 393-403.
    • (1988) J. Org. Chem. , vol.53 , pp. 2390-2392
    • Knochel, P.1    Yeh, M.C.P.2    Berk, S.C.3    Talbert, J.4
  • 28
    • 0002249396 scopus 로고    scopus 로고
    • P. Knochel, M. C. P. Yeh, S. C. Berk, J. Talbert, J. Org. Chem. 1988, 53, 2390-2392; L. Micouin, P. Knochel, Synlett 1997, 327-328; P. Knochel, R. D. Singer, Chem. Rev. 1993, 93, 2117-2188; P. Knochel, Synlett 1995, 393-403.
    • (1997) Synlett , pp. 327-328
    • Micouin, L.1    Knochel, P.2
  • 29
    • 4243489506 scopus 로고
    • P. Knochel, M. C. P. Yeh, S. C. Berk, J. Talbert, J. Org. Chem. 1988, 53, 2390-2392; L. Micouin, P. Knochel, Synlett 1997, 327-328; P. Knochel, R. D. Singer, Chem. Rev. 1993, 93, 2117-2188; P. Knochel, Synlett 1995, 393-403.
    • (1993) Chem. Rev. , vol.93 , pp. 2117-2188
    • Knochel, P.1    Singer, R.D.2
  • 30
    • 0003170224 scopus 로고
    • P. Knochel, M. C. P. Yeh, S. C. Berk, J. Talbert, J. Org. Chem. 1988, 53, 2390-2392; L. Micouin, P. Knochel, Synlett 1997, 327-328; P. Knochel, R. D. Singer, Chem. Rev. 1993, 93, 2117-2188; P. Knochel, Synlett 1995, 393-403.
    • (1995) Synlett , pp. 393-403
    • Knochel, P.1
  • 31
    • 0344015392 scopus 로고    scopus 로고
    • note
    • [14]
  • 34
    • 0000154154 scopus 로고
    • J. Schwartz, J. A. Labinge, Angew. Chem. 1976, 88, 402-409; Angew. Chem. Int. Ed. Engl. 1976, 15, 333-340; J. A. Labinger in Comprehensive Organic Synthesis, Vol. 8 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 667-702.
    • (1976) Angew. Chem. , vol.88 , pp. 402-409
    • Schwartz, J.1    Labinge, J.A.2
  • 35
    • 84982433710 scopus 로고
    • J. Schwartz, J. A. Labinge, Angew. Chem. 1976, 88, 402-409; Angew. Chem. Int. Ed. Engl. 1976, 15, 333-340; J. A. Labinger in Comprehensive Organic Synthesis, Vol. 8 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 667-702.
    • (1976) Angew. Chem. Int. Ed. Engl. , vol.15 , pp. 333-340
  • 36
    • 0000395519 scopus 로고
    • (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford
    • J. Schwartz, J. A. Labinge, Angew. Chem. 1976, 88, 402-409; Angew. Chem. Int. Ed. Engl. 1976, 15, 333-340; J. A. Labinger in Comprehensive Organic Synthesis, Vol. 8 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 667-702.
    • (1991) Comprehensive Organic Synthesis, Vol. 8 , vol.8 , pp. 667-702
    • Labinger, J.A.1


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