메뉴 건너뛰기




Volumn 42, Issue 17, 2003, Pages 1900-1923

Recent developments in olefin cross-metathesis

Author keywords

Cross metathesis; Homogeneous catalysis; Olefins; Ring opening metathesis; Synthetic methods

Indexed keywords

CATALYSIS; CATALYSTS; CHEMICAL BONDS; OLEFINS; SYNTHESIS (CHEMICAL);

EID: 0038215596     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200200556     Document Type: Review
Times cited : (1256)

References (196)
  • 1
    • 0034746687 scopus 로고    scopus 로고
    • For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
    • (2001) Acc. Chem. Res. , vol.34 , pp. 18-29
    • Trnka, T.M.1    Grubbs, R.H.2
  • 2
    • 0000785058 scopus 로고    scopus 로고
    • For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
    • (2000) Angew. Chem. , vol.112 , pp. 3140-3172
    • Fürstner, A.1
  • 3
    • 85007633292 scopus 로고    scopus 로고
    • For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3012-3043
  • 4
    • 0034616213 scopus 로고    scopus 로고
    • For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
    • (2000) Chem. Commun. , pp. 519-529
    • Roy, R.1    Das, S.K.2
  • 5
    • 0001811974 scopus 로고    scopus 로고
    • For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
    • (1999) Aldrichimica Acta , vol.32 , pp. 75-90
    • Philips, A.J.1    Abell, A.D.2
  • 6
    • 28244440935 scopus 로고    scopus 로고
    • For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
    • (1998) J. Chem. Soc. Perkin Trans. 1 , pp. 371-388
    • Armstrong, S.K.1
  • 7
    • 0032580376 scopus 로고    scopus 로고
    • For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
    • (1998) Tetrahedron , vol.54 , pp. 4413-4450
    • Grubbs, R.H.1    Chang, S.2
  • 8
    • 0032514162 scopus 로고    scopus 로고
    • For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
    • (1998) J. Mol. Catal. A , vol.133 , pp. 1-16
    • Ivin, K.J.1
  • 9
    • 0003464699 scopus 로고    scopus 로고
    • (Ed.: A. Fürstner), Springer, Berlin
    • For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
    • (1998) Alkene Metathesis in Organic Synthesis
  • 10
    • 0032514226 scopus 로고    scopus 로고
    • For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
    • (1998) J. Mol. Catal. A , vol.133 , pp. 29-40
    • Randall, M.L.1    Snapper, M.L.2
  • 11
    • 0000063152 scopus 로고    scopus 로고
    • For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
    • (1997) Angew. Chem. , vol.109 , pp. 2124-2144
    • Schuster, M.1    Blechert, S.2
  • 12
    • 0030771019 scopus 로고    scopus 로고
    • For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2036-2055
  • 13
    • 0000868479 scopus 로고
    • For the first proposal of the currently accepted mechanism, see: J. L. Hérisson, Y. Chauvin, Makromol. Chem. 1970, 141, 161-176.
    • (1970) Makromol. Chem. , vol.141 , pp. 161-176
    • Hérisson, J.L.1    Chauvin, Y.2
  • 15
    • 0038206382 scopus 로고
    • Company publication
    • b) Shell International Chemical Company, SHOP - Linear Alpha Olefins (Company publication), 1982.
    • (1982) SHOP - Linear Alpha Olefins
  • 16
    • 84891018968 scopus 로고
    • Phillips Petroleum Company, Hydrocarbon Process 1967, 46, 232.
    • (1967) Hydrocarbon Process , vol.46 , pp. 232
  • 24
    • 0029903708 scopus 로고    scopus 로고
    • S. Blechert, M. Schuster, J. Pernerstorfer, Angew. Chem. 1996, 108, 2111-2112; Angew. Chem. Int. Ed. Engl. 1996, 35, 1979-1980.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 1979-1980
  • 32
    • 0038545128 scopus 로고    scopus 로고
    • For the extension of this methodology to include one-pot CM/allylboration reactions, see: S. D. Goldberg, R. H. Grubbs, Angew. Chem. 2002, 114, 835-838; Angew. Chem. Int. Ed. 2002, 41, 807-810.
    • (2002) Angew. Chem. , vol.114 , pp. 835-838
    • Goldberg, S.D.1    Grubbs, R.H.2
  • 33
    • 0036495555 scopus 로고    scopus 로고
    • For the extension of this methodology to include one-pot CM/allylboration reactions, see: S. D. Goldberg, R. H. Grubbs, Angew. Chem. 2002, 114, 835-838; Angew. Chem. Int. Ed. 2002, 41, 807-810.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 807-810
  • 34
    • 0000681082 scopus 로고    scopus 로고
    • For background information on the roles of methylidene and alkylidene intermediates derived from 6 in metathesis, see: R. H. Grubbs, M. Ulman, Organometallics 1998, 17, 2484-2489.
    • (1998) Organometallics , vol.17 , pp. 2484-2489
    • Grubbs, R.H.1    Ulman, M.2
  • 38
  • 47
    • 85007628511 scopus 로고    scopus 로고
    • note
    • [32]
  • 49
    • 0037009018 scopus 로고    scopus 로고
    • A. K. Chatterjee, R. H. Grubbs, Angew. Chem. 2002, 114, 3304-3306; Angew. Chem. Int. Ed. 2002, 41, 3171-3174.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 3171-3174
  • 53
    • 0035794963 scopus 로고    scopus 로고
    • T.-L. Choi, A. K. Chatterjee, R. H. Grubbs, Angew. Chem. 2001, 113, 1317-1319; Angew. Chem. Int. Ed. 2001, 40, 1277-1279.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 1277-1279
  • 64
    • 0038206375 scopus 로고    scopus 로고
    • For early examples involving RCM reactions, see: a) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; b) A. Ffirstner, K. Langemann, Synthesis 1997, 792-803; c) G. C. Fu, R. H. Grubbs, J. Am. Chem. Soc. 1992, 114, 7324-7325.
    • (1996) J. Org. Chem. , vol.61 , pp. 3942-3943
    • Fürstner, A.1    Langemann, K.2
  • 65
    • 0030857814 scopus 로고    scopus 로고
    • For early examples involving RCM reactions, see: a) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; b) A. Ffirstner, K. Langemann, Synthesis 1997, 792-803; c) G. C. Fu, R. H. Grubbs, J. Am. Chem. Soc. 1992, 114, 7324-7325.
    • (1997) Synthesis , pp. 792-803
    • Ffirstner, A.1    Langemann, K.2
  • 66
    • 0000587503 scopus 로고
    • For early examples involving RCM reactions, see: a) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; b) A. Ffirstner, K. Langemann, Synthesis 1997, 792-803; c) G. C. Fu, R. H. Grubbs, J. Am. Chem. Soc. 1992, 114, 7324-7325.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 7324-7325
    • Fu, G.C.1    Grubbs, R.H.2
  • 76
    • 0033917770 scopus 로고    scopus 로고
    • For an example involving vinylsilacyclobutanes, see: S. E. Denmark, Z. Wang, Synthesis 2000, 999-1003.
    • (2000) Synthesis , pp. 999-1003
    • Denmark, S.E.1    Wang, Z.2
  • 78
    • 0034700583 scopus 로고    scopus 로고
    • It has been shown that the metallacyclobutane intermediates derived from vinyltrialkylsilanes undergo metathesis-terminating β-silyl-elimination reactions to a much greater extent than do analogous vinyltrialkoxysilane-derived intermediates; for a discussion, see: C. Pietraszuk, H. Fischer, Chem. Commun. 2000, 2463-2464; C. Pietraszuk, H. Fischer, Organometallics 2001, 20, 4641-4646.
    • (2000) Chem. Commun. , pp. 2463-2464
    • Pietraszuk, C.1    Fischer, H.2
  • 79
    • 0035969288 scopus 로고    scopus 로고
    • It has been shown that the metallacyclobutane intermediates derived from vinyltrialkylsilanes undergo metathesis-terminating β-silyl-elimination reactions to a much greater extent than do analogous vinyltrialkoxysilane-derived intermediates; for a discussion, see: C. Pietraszuk, H. Fischer, Chem. Commun. 2000, 2463-2464; C. Pietraszuk, H. Fischer, Organometallics 2001, 20, 4641-4646.
    • (2001) Organometallics , vol.20 , pp. 4641-4646
    • Pietraszuk, C.1    Fischer, H.2
  • 101
    • 0001254655 scopus 로고    scopus 로고
    • For the first reports of ruthenium-catalyzed ROM-CM of norbornene and oxanorbornene, see: a) M. F. Schneider, S. Blechert, Angew. Chem. 1996, 108, 479-481; Angew. Chem. Int. Ed. Engl. 1996, 35, 411-413; b) M. F. Schneider, N. Lucas, J. Velder, S. Blechert, Angew. Chem. 1997,109, 257-259; Angew. Chem. Int. Ed. Engl. 1997, 36, 257-258.
    • (1996) Angew. Chem. , vol.108 , pp. 479-481
    • Schneider, M.F.1    Blechert, S.2
  • 102
    • 33748248553 scopus 로고    scopus 로고
    • For the first reports of ruthenium-catalyzed ROM-CM of norbornene and oxanorbornene, see: a) M. F. Schneider, S. Blechert, Angew. Chem. 1996, 108, 479-481; Angew. Chem. Int. Ed. Engl. 1996, 35, 411-413; b) M. F. Schneider, N. Lucas, J. Velder, S. Blechert, Angew. Chem. 1997,109, 257-259; Angew. Chem. Int. Ed. Engl. 1997, 36, 257-258.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 411-413
  • 103
    • 0030971552 scopus 로고    scopus 로고
    • For the first reports of ruthenium-catalyzed ROM-CM of norbornene and oxanorbornene, see: a) M. F. Schneider, S. Blechert, Angew. Chem. 1996, 108, 479-481; Angew. Chem. Int. Ed. Engl. 1996, 35, 411-413; b) M. F. Schneider, N. Lucas, J. Velder, S. Blechert, Angew. Chem. 1997,109, 257-259; Angew. Chem. Int. Ed. Engl. 1997, 36, 257-258.
    • (1997) Angew. Chem. , vol.109 , pp. 257-259
    • Schneider, M.F.1    Lucas, N.2    Velder, J.3    Blechert, S.4
  • 104
    • 0030971552 scopus 로고    scopus 로고
    • For the first reports of ruthenium-catalyzed ROM-CM of norbornene and oxanorbornene, see: a) M. F. Schneider, S. Blechert, Angew. Chem. 1996, 108, 479-481; Angew. Chem. Int. Ed. Engl. 1996, 35, 411-413; b) M. F. Schneider, N. Lucas, J. Velder, S. Blechert, Angew. Chem. 1997,109, 257-259; Angew. Chem. Int. Ed. Engl. 1997, 36, 257-258.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 257-258
  • 116
    • 0035793845 scopus 로고    scopus 로고
    • For a short review of asymmetric olefin metathesis, see: A. H. Hoveyda, R. R. Schrock, Chem. Eur. J. 2001, 7, 945-950.
    • (2001) Chem. Eur. J. , vol.7 , pp. 945-950
    • Hoveyda, A.H.1    Schrock, R.R.2
  • 122
    • 0036495319 scopus 로고    scopus 로고
    • H. Wakamatsu, S. Blechert, Angew. Chem. 2002, 114, 832-834; Angew. Chem. Int. Ed. 2002, 41, 794-796.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 794-796
  • 123
  • 124
    • 0037007937 scopus 로고    scopus 로고
    • H. Wakamatsu, S. Blechert, Angew. Chem. 2002, 114, 2509-2511; Angew. Chem. Int. Ed. 2002, 41, 2403-2405.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 2403-2405
  • 129
    • 0000093498 scopus 로고    scopus 로고
    • For an example of ROM-CM using carbynehydridoruthenium complexes, see: W. Stüer, J. Wolf, H. Werner, P. Schwab, M. Schultz, Angew. Chem. 1998, 110, 3603-3605; Angew. Chem. Int. Ed. 1998, 37, 3421-3423.
    • (1998) Angew. Chem. , vol.110 , pp. 3603-3605
    • Stüer, W.1    Wolf, J.2    Werner, H.3    Schwab, P.4    Schultz, M.5
  • 130
    • 33745159285 scopus 로고    scopus 로고
    • For an example of ROM-CM using carbynehydridoruthenium complexes, see: W. Stüer, J. Wolf, H. Werner, P. Schwab, M. Schultz, Angew. Chem. 1998, 110, 3603-3605; Angew. Chem. Int. Ed. 1998, 37, 3421-3423.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 3421-3423
  • 131
    • 0001077342 scopus 로고    scopus 로고
    • For a similar example (see above) using water-soluble vinylidene and allenylidene complexes, see: M. Saoud, A. Romerosa, M. Peruzzini, Organometallics 2000, 19, 4005-4007.
    • (2000) Organometallics , vol.19 , pp. 4005-4007
    • Saoud, M.1    Romerosa, A.2    Peruzzini, M.3
  • 135
    • 0031467515 scopus 로고    scopus 로고
    • R. Stragies, M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2628-2630; Angew. Chem. Int. Ed. Engl. 1997, 36, 2518-2520.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2518-2520
  • 136
  • 139
    • 0037059439 scopus 로고    scopus 로고
    • Enyne metathesis with ethylene catalyzed by 6 was recently applied in the synthesis of natural products: a) M. Mori, K. Tonogaki, N. Nishiguchi, J. Org. Chem. 2002, 67, 224-226; b) S. Rodríguez-Conesa, P. Candal, C. Jiménez, J. Rodríguez, Tetrahedron Lett. 2001, 42, 6699-6702.
    • (2002) J. Org. Chem. , vol.67 , pp. 224-226
    • Mori, M.1    Tonogaki, K.2    Nishiguchi, N.3
  • 140
    • 0035903955 scopus 로고    scopus 로고
    • Enyne metathesis with ethylene catalyzed by 6 was recently applied in the synthesis of natural products: a) M. Mori, K. Tonogaki, N. Nishiguchi, J. Org. Chem. 2002, 67, 224-226; b) S. Rodríguez-Conesa, P. Candal, C. Jiménez, J. Rodríguez, Tetrahedron Lett. 2001, 42, 6699-6702.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 6699-6702
    • Rodríguez-Conesa, S.1    Candal, P.2    Jiménez, C.3    Rodríguez, J.4
  • 144
    • 85007640198 scopus 로고    scopus 로고
    • note
    • The butadiene products from these reactions can also be used in nickel-catalyzed [4+4] cycloadditions; see: reference [102].
  • 157
    • 0034671741 scopus 로고    scopus 로고
    • H. Katayama, H. Urushima, T. Nishioka, C. Wada, M. Nagao, F. Ozawa, Angew. Chem. 2000, 112, 4687-4689; Angew. Chem. Int. Ed. 2000, 39, 4513-4515.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 4513-4515
  • 165
    • 0001847655 scopus 로고    scopus 로고
    • For an early example of RCM-mediated cleavage from a solid support, see: J.-U. Peters, S. Blechert, Synlett 1997, 348-350.
    • (1997) Synlett , pp. 348-350
    • Peters, J.-U.1    Blechert, S.2
  • 166
    • 0032706852 scopus 로고    scopus 로고
    • For an example of RCM-mediated cleavage in carbohydrate synthesis, see: L. Knerr, R. R. Schmidt, Synlett 1999, 11, 1802-1804.
    • (1999) Synlett , vol.11 , pp. 1802-1804
    • Knerr, L.1    Schmidt, R.R.2
  • 174
    • 0033603294 scopus 로고    scopus 로고
    • Complex 155 is the immobilized version of 1, the first active NHC catalyst; for background literature on the development of this system, see: a) L. Ackermann, A. Fürstner, T. Weskamp, F. J. Kohl, W. A. Herrmann, Tetrahedron Lett. 1999, 40, 4787-4790; b) J. Huang, E. D. Stevens, S. P. Nolan, J. L. Pedersen, J. Am. Chem. Soc. 1999, 121, 2674-2678; c) M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 2247-2250.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 4787-4790
    • Ackermann, L.1    Fürstner, A.2    Weskamp, T.3    Kohl, F.J.4    Herrmann, W.A.5
  • 175
    • 0033620417 scopus 로고    scopus 로고
    • Complex 155 is the immobilized version of 1, the first active NHC catalyst; for background literature on the development of this system, see: a) L. Ackermann, A. Fürstner, T. Weskamp, F. J. Kohl, W. A. Herrmann, Tetrahedron Lett. 1999, 40, 4787-4790; b) J. Huang, E. D. Stevens, S. P. Nolan, J. L. Pedersen, J. Am. Chem. Soc. 1999, 121, 2674-2678; c) M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 2247-2250.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 2674-2678
    • Huang, J.1    Stevens, E.D.2    Nolan, S.P.3    Pedersen, J.L.4
  • 176
    • 0033582991 scopus 로고    scopus 로고
    • Complex 155 is the immobilized version of 1, the first active NHC catalyst; for background literature on the development of this system, see: a) L. Ackermann, A. Fürstner, T. Weskamp, F. J. Kohl, W. A. Herrmann, Tetrahedron Lett. 1999, 40, 4787-4790; b) J. Huang, E. D. Stevens, S. P. Nolan, J. L. Pedersen, J. Am. Chem. Soc. 1999, 121, 2674-2678; c) M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 2247-2250.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2247-2250
    • Scholl, M.1    Trnka, T.M.2    Morgan, J.P.3    Grubbs, R.H.4
  • 178
    • 0034602069 scopus 로고    scopus 로고
    • S. C. Schürer, S. Gessler, N. Buschmann, S. Blechert, Angew. Chem. 2000, 112, 4062-4065; Angew. Chem. Int. Ed. 2000, 39, 3898-3901.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3898-3901
  • 182
    • 4243081008 scopus 로고    scopus 로고
    • Grubbs has prepared water-soluble catalysts that promote living ROMP and RCM reactions in aqueous and methanolic solutions (these species were not CM-active); for details of this pioneering work, see: a) B. Mohr, D. M. Lynn; R. H. Grubbs, Organometallics 1996, 15, 4317-4325; b) D. M. Lynn, B. Mohr, L. M. Henling, M. W. Day, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 6601-6609; c) D. M. Lynn, B. Mohr, R. H. Grubbs, J. Am. Chem. Soc. 1998, 120, 1627-1628; d) T. A. Kirkland, D. M. Lynn, R. H. Grubbs, J. Org. Chem. 1998, 63, 9904-9909.
    • (1996) Organometallics , vol.15 , pp. 4317-4325
    • Mohr, B.1    Lynn, D.M.2    Grubbs, R.H.3
  • 183
    • 0034686682 scopus 로고    scopus 로고
    • Grubbs has prepared water-soluble catalysts that promote living ROMP and RCM reactions in aqueous and methanolic solutions (these species were not CM-active); for details of this pioneering work, see: a) B. Mohr, D. M. Lynn; R. H. Grubbs, Organometallics 1996, 15, 4317-4325; b) D. M. Lynn, B. Mohr, L. M. Henling, M. W. Day, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 6601-6609; c) D. M. Lynn, B. Mohr, R. H. Grubbs, J. Am. Chem. Soc. 1998, 120, 1627-1628; d) T. A. Kirkland, D. M. Lynn, R. H. Grubbs, J. Org. Chem. 1998, 63, 9904-9909.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 6601-6609
    • Lynn, D.M.1    Mohr, B.2    Henling, L.M.3    Day, M.W.4    Grubbs, R.H.5
  • 184
    • 0032564844 scopus 로고    scopus 로고
    • Grubbs has prepared water-soluble catalysts that promote living ROMP and RCM reactions in aqueous and methanolic solutions (these species were not CM-active); for details of this pioneering work, see: a) B. Mohr, D. M. Lynn; R. H. Grubbs, Organometallics 1996, 15, 4317-4325; b) D. M. Lynn, B. Mohr, L. M. Henling, M. W. Day, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 6601-6609; c) D. M. Lynn, B. Mohr, R. H. Grubbs, J. Am. Chem. Soc. 1998, 120, 1627-1628; d) T. A. Kirkland, D. M. Lynn, R. H. Grubbs, J. Org. Chem. 1998, 63, 9904-9909.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 1627-1628
    • Lynn, D.M.1    Mohr, B.2    Grubbs, R.H.3
  • 185
    • 0032567497 scopus 로고    scopus 로고
    • Grubbs has prepared water-soluble catalysts that promote living ROMP and RCM reactions in aqueous and methanolic solutions (these species were not CM-active); for details of this pioneering work, see: a) B. Mohr, D. M. Lynn; R. H. Grubbs, Organometallics 1996, 15, 4317-4325; b) D. M. Lynn, B. Mohr, L. M. Henling, M. W. Day, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 6601-6609; c) D. M. Lynn, B. Mohr, R. H. Grubbs, J. Am. Chem. Soc. 1998, 120, 1627-1628; d) T. A. Kirkland, D. M. Lynn, R. H. Grubbs, J. Org. Chem. 1998, 63, 9904-9909.
    • (1998) J. Org. Chem. , vol.63 , pp. 9904-9909
    • Kirkland, T.A.1    Lynn, D.M.2    Grubbs, R.H.3
  • 186
    • 85007625716 scopus 로고    scopus 로고
    • note
    • [141] this is a further example of the utility of 4a as a metathesis tool to complement benchmark catalyst 3, which is insoluble in MeOH.
  • 188
    • 0035915174 scopus 로고    scopus 로고
    • J. S. Kingsbury, S. B. Garber, J. M. Giftos, B. L. Gray, M. M. Okamoto, R. A. Farrer, J. T. Fourkas, A. H. Hoveyda, Angew. Chem. 2001, 113, 4381-4386; Angew. Chem. Int. Ed. 2001, 40, 4251-4256.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 4251-4256
  • 189
    • 0000740951 scopus 로고    scopus 로고
    • For a report concerning the immobilization of a ruthenium metathesis catalyst on monolithic material by ROM-CM, see: M. Mayr, B. Mayr, M. R. Buchmeiser, Angew. Chem. 2001, 113, 3957-3960; Angew. Chem. Int. Ed. 2001, 40, 3839-3842.
    • (2001) Angew. Chem. , vol.113 , pp. 3957-3960
    • Mayr, M.1    Mayr, B.2    Buchmeiser, M.R.3
  • 190
    • 0035887467 scopus 로고    scopus 로고
    • For a report concerning the immobilization of a ruthenium metathesis catalyst on monolithic material by ROM-CM, see: M. Mayr, B. Mayr, M. R. Buchmeiser, Angew. Chem. 2001, 113, 3957-3960; Angew. Chem. Int. Ed. 2001, 40, 3839-3842.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 3839-3842
  • 191
    • 0000466852 scopus 로고    scopus 로고
    • A resin-immobilized molybdenum catalyst capable of asymmetric ROM-CM was reported recently; however, recyclability was poor: K. C. Hultzsch, J. A. Jernelius, A. H. Hoveyda, R. R. Schrock, Angew. Chem. 2002, 114, 609-613; Angew. Chem. Int. Ed. 2002, 41, 589-593.
    • (2002) Angew. Chem. , vol.114 , pp. 609-613
    • Hultzsch, K.C.1    Jernelius, J.A.2    Hoveyda, A.H.3    Schrock, R.R.4
  • 192
    • 0037084020 scopus 로고    scopus 로고
    • A resin-immobilized molybdenum catalyst capable of asymmetric ROM-CM was reported recently; however, recyclability was poor: K. C. Hultzsch, J. A. Jernelius, A. H. Hoveyda, R. R. Schrock, Angew. Chem. 2002, 114, 609-613; Angew. Chem. Int. Ed. 2002, 41, 589-593.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 589-593
  • 193
    • 0000431168 scopus 로고    scopus 로고
    • Q. Yao, Angew. Chem. 2000, 112, 4060-4062; Angew. Chem. Int. Ed. 2000, 39, 3896-3898.
    • (2000) Angew. Chem. , vol.112 , pp. 4060-4062
    • Yao, Q.1
  • 194
    • 0034602042 scopus 로고    scopus 로고
    • Q. Yao, Angew. Chem. 2000, 112, 4060-4062; Angew. Chem. Int. Ed. 2000, 39, 3896-3898.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3896-3898
  • 196
    • 0037131458 scopus 로고    scopus 로고
    • S. J. Connon, A. M. Dunne, S. Blechert, Angew. Chem. 2002, 114, 3989-3993; Angew. Chem. Int. Ed. 2002, 41, 3835-3838.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 3835-3838


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.