메뉴 건너뛰기




Volumn 39, Issue 42, 1998, Pages 7705-7708

Cycloadditions of allylsilanes, part 13: Lewis acid-promoted stereospecific [2+2] cycloaddition of crotylsilanes and methyl propynoate

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; SILANE DERIVATIVE; TITANIUM DERIVATIVE;

EID: 0032532571     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01678-5     Document Type: Article
Times cited : (34)

References (51)
  • 2
    • 84961484227 scopus 로고
    • 2. Reviews: H. Sakurai, Pure Appl. Chem. 1982, 54, 1; A. Hosomi, Acc. Chem. Res. 1988, 21, 200; I. Fleming, J. Dunoguès, R. Smithers, Org. React. 1989, 37, 57; G. Majetich, in Organic Synthesis, Theory and Applications (Ed.: T Hudlicky), JAI Press, Greenwich (CT), 1989, Vol. 1, p. 173; C. E. Masse, J. S. Panek, Chem. Rev. 1995, 95, 1293; E. Langkopf, D. Schinzer, Chem. Rev. 1995, 95, 1375; I. Fleming, A. Barbero, D. Walter, Chem. Rev. 1997, 97, 2063.
    • (1982) Pure Appl. Chem. , vol.54 , pp. 1
    • Sakurai, H.1
  • 3
    • 33845278941 scopus 로고
    • 2. Reviews: H. Sakurai, Pure Appl. Chem. 1982, 54, 1; A. Hosomi, Acc. Chem. Res. 1988, 21, 200; I. Fleming, J. Dunoguès, R. Smithers, Org. React. 1989, 37, 57; G. Majetich, in Organic Synthesis, Theory and Applications (Ed.: T Hudlicky), JAI Press, Greenwich (CT), 1989, Vol. 1, p. 173; C. E. Masse, J. S. Panek, Chem. Rev. 1995, 95, 1293; E. Langkopf, D. Schinzer, Chem. Rev. 1995, 95, 1375; I. Fleming, A. Barbero, D. Walter, Chem. Rev. 1997, 97, 2063.
    • (1988) Acc. Chem. Res. , vol.21 , pp. 200
    • Hosomi, A.1
  • 4
    • 0002324898 scopus 로고
    • 2. Reviews: H. Sakurai, Pure Appl. Chem. 1982, 54, 1; A. Hosomi, Acc. Chem. Res. 1988, 21, 200; I. Fleming, J. Dunoguès, R. Smithers, Org. React. 1989, 37, 57; G. Majetich, in Organic Synthesis, Theory and Applications (Ed.: T Hudlicky), JAI Press, Greenwich (CT), 1989, Vol. 1, p. 173; C. E. Masse, J. S. Panek, Chem. Rev. 1995, 95, 1293; E. Langkopf, D. Schinzer, Chem. Rev. 1995, 95, 1375; I. Fleming, A. Barbero, D. Walter, Chem. Rev. 1997, 97, 2063.
    • (1989) Org. React. , vol.37 , pp. 57
    • Fleming, I.1    Dunoguès, J.2    Smithers, R.3
  • 5
    • 0001564839 scopus 로고
    • Ed.: T Hudlicky, JAI Press, Greenwich (CT)
    • 2. Reviews: H. Sakurai, Pure Appl. Chem. 1982, 54, 1; A. Hosomi, Acc. Chem. Res. 1988, 21, 200; I. Fleming, J. Dunoguès, R. Smithers, Org. React. 1989, 37, 57; G. Majetich, in Organic Synthesis, Theory and Applications (Ed.: T Hudlicky), JAI Press, Greenwich (CT), 1989, Vol. 1, p. 173; C. E. Masse, J. S. Panek, Chem. Rev. 1995, 95, 1293; E. Langkopf, D. Schinzer, Chem. Rev. 1995, 95, 1375; I. Fleming, A. Barbero, D. Walter, Chem. Rev. 1997, 97, 2063.
    • (1989) Organic Synthesis, Theory and Applications , vol.1 , pp. 173
    • Majetich, G.1
  • 6
    • 0343778881 scopus 로고
    • 2. Reviews: H. Sakurai, Pure Appl. Chem. 1982, 54, 1; A. Hosomi, Acc. Chem. Res. 1988, 21, 200; I. Fleming, J. Dunoguès, R. Smithers, Org. React. 1989, 37, 57; G. Majetich, in Organic Synthesis, Theory and Applications (Ed.: T Hudlicky), JAI Press, Greenwich (CT), 1989, Vol. 1, p. 173; C. E. Masse, J. S. Panek, Chem. Rev. 1995, 95, 1293; E. Langkopf, D. Schinzer, Chem. Rev. 1995, 95, 1375; I. Fleming, A. Barbero, D. Walter, Chem. Rev. 1997, 97, 2063.
    • (1995) Chem. Rev. , vol.95 , pp. 1293
    • Masse, C.E.1    Panek, J.S.2
  • 7
    • 0000986731 scopus 로고
    • 2. Reviews: H. Sakurai, Pure Appl. Chem. 1982, 54, 1; A. Hosomi, Acc. Chem. Res. 1988, 21, 200; I. Fleming, J. Dunoguès, R. Smithers, Org. React. 1989, 37, 57; G. Majetich, in Organic Synthesis, Theory and Applications (Ed.: T Hudlicky), JAI Press, Greenwich (CT), 1989, Vol. 1, p. 173; C. E. Masse, J. S. Panek, Chem. Rev. 1995, 95, 1293; E. Langkopf, D. Schinzer, Chem. Rev. 1995, 95, 1375; I. Fleming, A. Barbero, D. Walter, Chem. Rev. 1997, 97, 2063.
    • (1995) Chem. Rev. , vol.95 , pp. 1375
    • Langkopf, E.1    Schinzer, D.2
  • 8
    • 0000595175 scopus 로고    scopus 로고
    • 2. Reviews: H. Sakurai, Pure Appl. Chem. 1982, 54, 1; A. Hosomi, Acc. Chem. Res. 1988, 21, 200; I. Fleming, J. Dunoguès, R. Smithers, Org. React. 1989, 37, 57; G. Majetich, in Organic Synthesis, Theory and Applications (Ed.: T Hudlicky), JAI Press, Greenwich (CT), 1989, Vol. 1, p. 173; C. E. Masse, J. S. Panek, Chem. Rev. 1995, 95, 1293; E. Langkopf, D. Schinzer, Chem. Rev. 1995, 95, 1375; I. Fleming, A. Barbero, D. Walter, Chem. Rev. 1997, 97, 2063.
    • (1997) Chem. Rev. , vol.97 , pp. 2063
    • Fleming, I.1    Barbero, A.2    Walter, D.3
  • 13
    • 33748819544 scopus 로고
    • (c) H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, Angew. Chem. 1993, 105, 1104; Angew. Chem. Int. Ed. Engl. 1993, 32, 1081;
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 1081
  • 25
    • 33748231662 scopus 로고
    • 5. H.-J. Knölker, G. Baum, R. Graf, Angew. Chem. 1994, 106, 1705; Angew. Chem. Int. Ed. Engl. 1994, 33, 1612.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 1612
  • 26
    • 0027145040 scopus 로고
    • 6. M. Hojo, K. Tomita, Y. Hirohara, A. Hosomi, Tetrahedron Lett. 1993, 34, 8123; H. Monti, G. Audran, J.-P. Monti, G. Léandri, Synlett 1994, 403; G. P. Brengel, C. Rithner, A. I. Meyers, J. Org. Chem. 1994, 59, 5144; W. S. Murphy, D. Neville, Tetrahedron Lett. 1997, 38, 7933.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 8123
    • Hojo, M.1    Tomita, K.2    Hirohara, Y.3    Hosomi, A.4
  • 27
    • 0003142596 scopus 로고
    • 6. M. Hojo, K. Tomita, Y. Hirohara, A. Hosomi, Tetrahedron Lett. 1993, 34, 8123; H. Monti, G. Audran, J.-P. Monti, G. Léandri, Synlett 1994, 403; G. P. Brengel, C. Rithner, A. I. Meyers, J. Org. Chem. 1994, 59, 5144; W. S. Murphy, D. Neville, Tetrahedron Lett. 1997, 38, 7933.
    • (1994) Synlett , pp. 403
    • Monti, H.1    Audran, G.2    Monti, J.-P.3    Léandri, G.4
  • 28
    • 0000327520 scopus 로고
    • 6. M. Hojo, K. Tomita, Y. Hirohara, A. Hosomi, Tetrahedron Lett. 1993, 34, 8123; H. Monti, G. Audran, J.-P. Monti, G. Léandri, Synlett 1994, 403; G. P. Brengel, C. Rithner, A. I. Meyers, J. Org. Chem. 1994, 59, 5144; W. S. Murphy, D. Neville, Tetrahedron Lett. 1997, 38, 7933.
    • (1994) J. Org. Chem. , vol.59 , pp. 5144
    • Brengel, G.P.1    Rithner, C.2    Meyers, A.I.3
  • 29
    • 0030859733 scopus 로고    scopus 로고
    • 6. M. Hojo, K. Tomita, Y. Hirohara, A. Hosomi, Tetrahedron Lett. 1993, 34, 8123; H. Monti, G. Audran, J.-P. Monti, G. Léandri, Synlett 1994, 403; G. P. Brengel, C. Rithner, A. I. Meyers, J. Org. Chem. 1994, 59, 5144; W. S. Murphy, D. Neville, Tetrahedron Lett. 1997, 38, 7933.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 7933
    • Murphy, W.S.1    Neville, D.2
  • 31
    • 0001892550 scopus 로고    scopus 로고
    • 7. T. Akiyama, M. Kirino, Chem. Lett. 1995, 723; T. Akiyama, M. Yamanaka, Synlett 1996, 1095.
    • (1996) Synlett , pp. 1095
    • Akiyama, T.1    Yamanaka, M.2
  • 33
    • 0010410142 scopus 로고    scopus 로고
    • 9. For recent reviews, see: I. Fleming, Chemtracts-Organic Chemistry 1996, 9, 1; G. R. Jones, Y. Landais, Tetrahedron 1996, 52, 7599; K. Tamao, in Advances in Silicon Chemistry, JAI Press, Greenwich (CT), 1996, Vol. 3, p. 1.
    • (1996) Chemtracts-organic Chemistry , vol.9 , pp. 1
  • 34
    • 0030007621 scopus 로고    scopus 로고
    • 9. For recent reviews, see: I. Fleming, Chemtracts-Organic Chemistry 1996, 9, 1; G. R. Jones, Y. Landais, Tetrahedron 1996, 52, 7599; K. Tamao, in Advances in Silicon Chemistry, JAI Press, Greenwich (CT), 1996, Vol. 3, p. 1.
    • (1996) Tetrahedron , vol.52 , pp. 7599
    • Jones, G.R.1    Landais, Y.2
  • 35
    • 0002437012 scopus 로고    scopus 로고
    • JAI Press, Greenwich (CT)
    • 9. For recent reviews, see: I. Fleming, Chemtracts-Organic Chemistry 1996, 9, 1; G. R. Jones, Y. Landais, Tetrahedron 1996, 52, 7599; K. Tamao, in Advances in Silicon Chemistry, JAI Press, Greenwich (CT), 1996, Vol. 3, p. 1.
    • (1996) Advances in Silicon Chemistry , vol.3 , pp. 1
    • Tamao, K.1
  • 39
    • 18844399957 scopus 로고
    • 13. M. Schlosser, J. Hartmann, V. David, Helv. Chim. Acta 1974, 57, 1567; M. Schlosser, J. Hartmann, J. Am. Chem. Soc. 1976, 98, 4674; reviews: M. Schlosser, Pure Appl. Chem. 1988, 60, 1627; M. Schlosser, O. Desponds, R. Lehmann, E. Moret, G. Rauchschwalbe, Tetrahedron 1993, 49, 10175; M. Schlosser, in Organometallics in Synthesis-A Manual (Ed.: M. Schlosser), Wiley, Chichester, 1994, p. 1.
    • (1974) Helv. Chim. Acta , vol.57 , pp. 1567
    • Schlosser, M.1    Hartmann, J.2    David, V.3
  • 40
    • 0001754294 scopus 로고
    • 13. M. Schlosser, J. Hartmann, V. David, Helv. Chim. Acta 1974, 57, 1567; M. Schlosser, J. Hartmann, J. Am. Chem. Soc. 1976, 98, 4674; reviews: M. Schlosser, Pure Appl. Chem. 1988, 60, 1627; M. Schlosser, O. Desponds, R. Lehmann, E. Moret, G. Rauchschwalbe, Tetrahedron 1993, 49, 10175; M. Schlosser, in Organometallics in Synthesis-A Manual (Ed.: M. Schlosser), Wiley, Chichester, 1994, p. 1.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 4674
    • Schlosser, M.1    Hartmann, J.2
  • 41
    • 84918129478 scopus 로고
    • 13. M. Schlosser, J. Hartmann, V. David, Helv. Chim. Acta 1974, 57, 1567; M. Schlosser, J. Hartmann, J. Am. Chem. Soc. 1976, 98, 4674; reviews: M. Schlosser, Pure Appl. Chem. 1988, 60, 1627; M. Schlosser, O. Desponds, R. Lehmann, E. Moret, G. Rauchschwalbe, Tetrahedron 1993, 49, 10175; M. Schlosser, in Organometallics in Synthesis-A Manual (Ed.: M. Schlosser), Wiley, Chichester, 1994, p. 1.
    • (1988) Pure Appl. Chem. , vol.60 , pp. 1627
    • Schlosser, M.1
  • 42
    • 0027429535 scopus 로고
    • 13. M. Schlosser, J. Hartmann, V. David, Helv. Chim. Acta 1974, 57, 1567; M. Schlosser, J. Hartmann, J. Am. Chem. Soc. 1976, 98, 4674; reviews: M. Schlosser, Pure Appl. Chem. 1988, 60, 1627; M. Schlosser, O. Desponds, R. Lehmann, E. Moret, G. Rauchschwalbe, Tetrahedron 1993, 49, 10175; M. Schlosser, in Organometallics in Synthesis-A Manual (Ed.: M. Schlosser), Wiley, Chichester, 1994, p. 1.
    • (1993) Tetrahedron , vol.49 , pp. 10175
    • Schlosser, M.1    Desponds, O.2    Lehmann, R.3    Moret, E.4    Rauchschwalbe, G.5
  • 43
    • 0002064932 scopus 로고
    • Ed.: M. Schlosser, Wiley, Chichester
    • 13. M. Schlosser, J. Hartmann, V. David, Helv. Chim. Acta 1974, 57, 1567; M. Schlosser, J. Hartmann, J. Am. Chem. Soc. 1976, 98, 4674; reviews: M. Schlosser, Pure Appl. Chem. 1988, 60, 1627; M. Schlosser, O. Desponds, R. Lehmann, E. Moret, G. Rauchschwalbe, Tetrahedron 1993, 49, 10175; M. Schlosser, in Organometallics in Synthesis-A Manual (Ed.: M. Schlosser), Wiley, Chichester, 1994, p. 1.
    • (1994) Organometallics in Synthesis-A Manual , pp. 1
    • Schlosser, M.1
  • 44
    • 85038550288 scopus 로고    scopus 로고
    • note
    • 3): δ = 0.68 (dd, J = 15.6, 10.0, 1 H), 1.01-1.09 (m, 22 H), 1.10 (d, J = 7.2, 3 H), 2.90 (dq, J = 4.4, 7.2, 1 H), 3.25 (br dt, J = 10.0, 3.7, 1 H), 3.70 (s, 3 H), 6.75 (s, 1 H).
  • 45
    • 85038547916 scopus 로고    scopus 로고
    • note
    • 3): δ = 0.64 (dd, J = 15.2, 12.2, 1 H), 1.01-1.09 (m, 21 H), 1.17 (d, J = 7.8, 3 H), 1.35 (dd, J = 15.2, 2.2, 1 H), 2.34 (br q, J = 7.0, 1 H), 2.59 (ddd, J = 12.2, 1.9, 1.6, 1 H), 3.72 (s, 3 H), 6.75 (s, 1 H).
  • 46
    • 85038542856 scopus 로고    scopus 로고
    • note
    • 6): δ = 0.99-1.12 (m, 21 H), 1.62 (dd, J = 6.7, 1.6, 3 H), 2.19 (d, J = 9.4, 2 H), 3.46 (s, 3 H), 5.78 (dq, J = 15.5, 6.7, 1 H), 6.14 (t, J = 9.4, 1 H), 6.21 (dd, J = 15.5, 1.0, 1 H).
  • 47
    • 84943067491 scopus 로고
    • 17. J. Sauer, B. Schröder, Chem. Ber. 1967, 100, 678; R. C. Cookson, S. S. H. Gilani, I. D. R. Stevens, J. Chem. Soc. C 1967, 1905; C. J. Moody, Adv. Heterocycl. Chem. 1982, 30, 1.
    • (1967) Chem. Ber. , vol.100 , pp. 678
    • Sauer, J.1    Schröder, B.2
  • 49
    • 0001863934 scopus 로고
    • 17. J. Sauer, B. Schröder, Chem. Ber. 1967, 100, 678; R. C. Cookson, S. S. H. Gilani, I. D. R. Stevens, J. Chem. Soc. C 1967, 1905; C. J. Moody, Adv. Heterocycl. Chem. 1982, 30, 1.
    • (1982) Adv. Heterocycl. Chem. , vol.30 , pp. 1
    • Moody, C.J.1
  • 50
    • 85038549767 scopus 로고    scopus 로고
    • note
    • 2 (SHELXL-93); the program SCHAKAL-97 was used for the graphical representation of the crystal structure. Atomic coordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.