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Volumn 72, Issue 23, 2007, Pages 8648-8655

Exceptionally active yttrium-salen complexes for the catalyzed ring opening of epoxides by TMSCN and TMSN3

Author keywords

[No Author keywords available]

Indexed keywords

ALKOXIDE; CATALYST RATIOS; TUNABLE LIGAND SYSTEMS; YTTRIUM SALEN COMPLEXES;

EID: 35948944461     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo071076h     Document Type: Article
Times cited : (42)

References (43)
  • 3
    • 35948935339 scopus 로고    scopus 로고
    • The initial results on the yttrium-catalyzed opening of epoxycyclohexane and epoxycyclopentane are extracted from; Lin, M.-H. Yttrium-Catalyzed Reactions: Transacylation, Secondary Alcohol Resolution, Cyanosilylation of Ketones and Epoxides. Ph.D. Dissertation, The Ohio State University, 2002
    • The initial results on the yttrium-catalyzed opening of epoxycyclohexane and epoxycyclopentane are extracted from; Lin, M.-H. Yttrium-Catalyzed Reactions: Transacylation, Secondary Alcohol Resolution, Cyanosilylation of Ketones and Epoxides. Ph.D. Dissertation, The Ohio State University, 2002.
  • 4
    • 0029764025 scopus 로고    scopus 로고
    • For leading references, see, for TMSCN: (a) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668.
    • For leading references, see, for TMSCN: (a) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668.
  • 6
    • 23844530814 scopus 로고    scopus 로고
    • Addition of TMSCN to aziridines: Mita, T.; Fujimori, I.; Wada, R.; Wen, J.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 11252.
    • (c) Addition of TMSCN to aziridines: Mita, T.; Fujimori, I.; Wada, R.; Wen, J.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 11252.
  • 8
    • 0032481031 scopus 로고    scopus 로고
    • Addition of PhLi: Oguni, N.; Miyagi, Y.; Itoh, K. Tetrahedron Lett. 1998, 39, 9023.
    • (e) Addition of PhLi: Oguni, N.; Miyagi, Y.; Itoh, K. Tetrahedron Lett. 1998, 39, 9023.
  • 9
    • 35948990909 scopus 로고    scopus 로고
    • Addition of alkynyllithium reagents: Zhu, C.; Yang, M.; Sun, J.; Zhu, Y.; Pan, Y. Synlett 2004, 465.
    • (f) Addition of alkynyllithium reagents: Zhu, C.; Yang, M.; Sun, J.; Zhu, Y.; Pan, Y. Synlett 2004, 465.
  • 10
    • 0141605110 scopus 로고    scopus 로고
    • Addition of TMSCN with ephedrine Ga and In complexes gives isonitriles: Yuan, F.; Zhu, C.; Sun, J.; Liu, Y.; Pan, Y. J. Organomet. Chem. 2003, 682, 102.
    • (g) Addition of TMSCN with ephedrine Ga and In complexes gives isonitriles: Yuan, F.; Zhu, C.; Sun, J.; Liu, Y.; Pan, Y. J. Organomet. Chem. 2003, 682, 102.
  • 11
    • 13944249839 scopus 로고    scopus 로고
    • For a report of TMSCN-mediated ring opening of α,β-epoxy carboxamides catalyzed by Sm(III), see: Tosaki, S.; Tsuji, R.; Oshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 2147.
    • (h) For a report of TMSCN-mediated ring opening of α,β-epoxy carboxamides catalyzed by Sm(III), see: Tosaki, S.; Tsuji, R.; Oshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 2147.
  • 12
    • 0033920416 scopus 로고    scopus 로고
    • For a review of asymmetric ring opening reactions of epoxides, see
    • For a review of asymmetric ring opening reactions of epoxides, see: Jacobsen, E. Acc. Chem. Res. 2000, 33, 421.
    • (2000) Acc. Chem. Res , vol.33 , pp. 421
    • Jacobsen, E.1
  • 15
    • 0033920416 scopus 로고    scopus 로고
    • 3 to epoxycyclohexane. (a) See: Jacobsen, E. Acc. Chem. Res. 2000, 33, 421 and references cited therein.
    • 3 to epoxycyclohexane. (a) See: Jacobsen, E. Acc. Chem. Res. 2000, 33, 421 and references cited therein.
  • 16
    • 0032556244 scopus 로고    scopus 로고
    • 10780. Footnote 7 of this paper is especially relevant to the present discussion
    • (b) Konsler, R. G.; Karl, J.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 10780. Footnote 7 of this paper is especially relevant to the present discussion.
    • (1998) J. Am. Chem. Soc , vol.120
    • Konsler, R.G.1    Karl, J.2    Jacobsen, E.N.3
  • 17
    • 0025131291 scopus 로고    scopus 로고
    • Anecdotal evidence for such inhibition by chloride ion can be found in the early experiments of Utimoto who showed that lanthanide chlorides are poor catalysts for the reaction between epoxycyclohexane and TMSCN. See: Matsubara, S, Onishi, H, Utimoto, K. Tetrahedron Lett. 1990, 31, 6209
    • Anecdotal evidence for such inhibition by chloride ion can be found in the early experiments of Utimoto who showed that lanthanide chlorides are poor catalysts for the reaction between epoxycyclohexane and TMSCN. See: Matsubara, S.; Onishi, H.; Utimoto, K. Tetrahedron Lett. 1990, 31, 6209.
  • 20
    • 35949003664 scopus 로고    scopus 로고
    • For full experimental details, including the preparation and use of the ligands listed in Figure 1, see the Supporting Information. Details of the spectroscopic and chromatographic identification of compounds are also included there.
    • For full experimental details, including the preparation and use of the ligands listed in Figure 1, see the Supporting Information. Details of the spectroscopic and chromatographic identification of compounds are also included there.
  • 22
    • 35948933552 scopus 로고    scopus 로고
    • Jacobsen has reported that 1 mol, of a monomeric (salen)Cr-N3 complex is needed effect the opening of epoxycyclopentane with TMS-N 3 under these conditions see ref 6
    • 3 under these conditions (see ref 6).
  • 23
    • 35948966885 scopus 로고    scopus 로고
    • Crystallographic details for 6 and a figure representing thermal ellipsoids are included in the Supporting Information.
    • Crystallographic details for 6 and a figure representing thermal ellipsoids are included in the Supporting Information.
  • 24
    • 0035793293 scopus 로고    scopus 로고
    • 2: Mascarenhas, C. M.; Miller, S. P.; White, P. S.; Morken, J. P. Angew. Chem., Int. Ed. 2001, 40, 601.
    • 2: Mascarenhas, C. M.; Miller, S. P.; White, P. S.; Morken, J. P. Angew. Chem., Int. Ed. 2001, 40, 601.
  • 28
    • 0037138628 scopus 로고    scopus 로고
    • An alkoxide bridged dimer: Ovitt, T. M, Coates, G. W. J. Am. Chem. Soc. 2002, 124, 1316. Al
    • (e) An alkoxide bridged dimer: Ovitt, T. M.; Coates, G. W. J. Am. Chem. Soc. 2002, 124, 1316. Al:
  • 29
    • 0035907043 scopus 로고    scopus 로고
    • Al(L4)X: Evans, D. A.; Janey, J. M.; Magomedov, N.; Tedrow, J. S. Angew. Chem., Int. Ed. 2001, 40, 1884.
    • (f) Al(L4)X: Evans, D. A.; Janey, J. M.; Magomedov, N.; Tedrow, J. S. Angew. Chem., Int. Ed. 2001, 40, 1884.
  • 30
    • 0001515027 scopus 로고    scopus 로고
    • In the ring-opening reaction of epoxycyclohexane by TMSCN, selective formation of a nitrile or an isonitrile product can be achieved by the choice of Lewis acids. Thus, Zn, Pd, Sn, In, and Ga salts give the isonitrile, whereas Ca, Mg, Zn, Y, Ti, and most lanthanide salts give the nitrile. Isonitrile: (a) Gassman, P. G, Guggenheim, T. L. J. Am. Chem. Soc. 1982, 104, 5849
    • In the ring-opening reaction of epoxycyclohexane by TMSCN, selective formation of a nitrile or an isonitrile product can be achieved by the choice of Lewis acids. Thus, Zn, Pd, Sn, In, and Ga salts give the isonitrile, whereas Ca, Mg, Zn, Y, Ti, and most lanthanide salts give the nitrile. Isonitrile: (a) Gassman, P. G.; Guggenheim, T. L. J. Am. Chem. Soc. 1982, 104, 5849.
  • 38
    • 0025131291 scopus 로고    scopus 로고
    • Matsubara, S.; Onishi, H.; Utimoto, K. Tetrahedron Lett. 1990, 31, 6209. See also refs 3a,b,g.
    • (i) Matsubara, S.; Onishi, H.; Utimoto, K. Tetrahedron Lett. 1990, 31, 6209. See also refs 3a,b,g.
  • 39
    • 1842528335 scopus 로고    scopus 로고
    • For IR spectroscopy of bridged nitrile/isonitrile complexes, see: (a) Sheng, T.; H. Vahrenkamp, H. Inorg. Chim. Acta 2004, 357, 1739.
    • For IR spectroscopy of bridged nitrile/isonitrile complexes, see: (a) Sheng, T.; H. Vahrenkamp, H. Inorg. Chim. Acta 2004, 357, 1739.


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