메뉴 건너뛰기




Volumn , Issue , 1985, Pages 247-308

On the Mechanism of Asymmetric Epoxidation with Titanium-Tartrate Catalysts

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY; SPEECH SYNTHESIS;

EID: 84941216140     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-08-092493-9.50013-X     Document Type: Chapter
Times cited : (315)

References (202)
  • 1
    • 0003978131 scopus 로고
    • Prentice-Hall, Englewood Cliffs, New Jersey, a. (reprinted by the American Chemical Society, 1976)
    • Morrison J.D., Mosher H.S. "Asymmetric Organic Reactions." 1976, Prentice-Hall, Englewood Cliffs, New Jersey, a. (reprinted by the American Chemical Society, 1976).
    • (1976) "Asymmetric Organic Reactions."
    • Morrison, J.D.1    Mosher, H.S.2
  • 5
    • 0002979638 scopus 로고
    • For more detailed reviews, see:
    • Boone J.R., Ashby E.C. Top. Stereochem. 1979, 11:53-95. b. For more detailed reviews, see:.
    • (1979) Top. Stereochem. , vol.11 , pp. 53-95
    • Boone, J.R.1    Ashby, E.C.2
  • 11
    • 0002451214 scopus 로고
    • For more recent transition state proposals
    • Anh N.T., Eisenstein O. Nouv. J. Chim. 1977, 1:61-70. g. For more recent transition state proposals, see:.
    • (1977) Nouv. J. Chim. , vol.1 , pp. 61-70
    • Anh, N.T.1    Eisenstein, O.2
  • 14
    • 0041879980 scopus 로고
    • and references cited therein
    • Robinson M.J.T. Tetrahedron 1974, 30:1499-1501. and references cited therein.
    • (1974) Tetrahedron , vol.30 , pp. 1499-1501
    • Robinson, M.J.T.1
  • 18
    • 0004165006 scopus 로고
    • Wiley (Interscience), New York, Chapter V; a.
    • Swern D. "Organic Peroxides," 1971, II. Wiley (Interscience), New York, Chapter V; a.
    • (1971) "Organic Peroxides," , vol.II
    • Swern, D.1
  • 20
    • 0000536803 scopus 로고
    • Dryuk G. Tetrahedron 1976, 32:2855-2866. c.
    • (1976) Tetrahedron , vol.32 , pp. 2855-2866
    • Dryuk, G.1
  • 28
    • 34250862346 scopus 로고
    • Chapter III
    • For an account of the events and reasoning leading up to the discovery of the asymmetric epoxidation process, see: Sharpless, K. B. (1984). Proc. Robert A. Welch Found. Conf. Chem. Res.27, Chapter III, pp. 59-89.
    • (1984) Proc. Robert A. Welch Found. Conf. Chem. Res. , vol.27 , pp. 59-89
    • Sharpless, K.B.1
  • 33
    • 0039001367 scopus 로고
    • Reidel Publ., Dordrecht, Netherlands, d. R. Ugo (Ed.)
    • Lyons J.E. "Aspects of Homogeneous Catalysis" 1977, 3:1-136. Reidel Publ., Dordrecht, Netherlands, d. R. Ugo (Ed.).
    • (1977) "Aspects of Homogeneous Catalysis" , vol.3 , pp. 1-136
    • Lyons, J.E.1
  • 78
    • 0020787109 scopus 로고
    • 17O-NMR measurements that a Mo(VI)-oxo-peroxo complex does not undergo exchange of oxo and peroxo oxygen atoms
    • 17O-NMR measurements that a Mo(VI)-oxo-peroxo complex does not undergo exchange of oxo and peroxo oxygen atoms.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 4922-4926
    • Postel, M.1    Brevard, C.2    Arzoumanian, H.3    Reiss, J.G.4
  • 89
    • 0001243532 scopus 로고
    • The more electron-deficient the metal, the more reactive is the coordinated alkyl peroxide group to nucleophilic attack. See ref. 8c, See also:
    • Strukul G., Michelin R.A., Orbell J.D., Randaccio L. Inorg. Chem. 1983, 22:3706-3713. b. The more electron-deficient the metal, the more reactive is the coordinated alkyl peroxide group to nucleophilic attack. See ref. 8c, p. 347. See also:.
    • (1983) Inorg. Chem. , vol.22 , pp. 3706-3713+347
    • Strukul, G.1    Michelin, R.A.2    Orbell, J.D.3    Randaccio, L.4
  • 135
    • 0006005163 scopus 로고
    • d; and references cited therein.
    • Marsman B., Wynberg H. J. Org. Chem. 1979, 44:2312-2314. d; and references cited therein.
    • (1979) J. Org. Chem. , vol.44 , pp. 2312-2314
    • Marsman, B.1    Wynberg, H.2
  • 140
    • 85021616692 scopus 로고
    • (W. Bartmann, and B. M. Trost, eds.), Workshop Conf. Hoechst, 14th, and references cited therein. Verlag Chemie, Weinheim.
    • Wynberg, H. (1983). In "Selectivity-A Goal for Synthetic Efficiency" (W. Bartmann, and B. M. Trost, eds.), Workshop Conf. Hoechst, 14th, pp. 365-375, and references cited therein. Verlag Chemie, Weinheim.
    • (1983) In "Selectivity-A Goal for Synthetic Efficiency" , pp. 365-375
    • Wynberg, H.1
  • 155
    • 85080310464 scopus 로고    scopus 로고
    • unpublished results.
    • Sharpless, K. B., unpublished results.
    • Sharpless, K.B.1
  • 156
    • 85080415677 scopus 로고
    • Ph. D. Dissertation, Stanford University, Stanford, California.
    • Woodard, S. S. (1981). Ph. D. Dissertation, Stanford University, Stanford, California.
    • (1981)
    • Woodard, S.S.1
  • 163
    • 0004079121 scopus 로고
    • For a general mathematical treatment of kinetic resolution and related processes, see:
    • Brandt J., Jochum C., Ugi I. Tetrahedron 1977, 33:1353-1363. For a general mathematical treatment of kinetic resolution and related processes, see:.
    • (1977) Tetrahedron , vol.33 , pp. 1353-1363
    • Brandt, J.1    Jochum, C.2    Ugi, I.3
  • 171
    • 33847799789 scopus 로고
    • This same general structure is shared by complexes of tartaric acid with Sb(III), As(III), Cu(II), and Cr(III) [; and references cited therein.
    • Robbins G.L., Tapscott R.E. Inorg. Chem. 1976, 15:154-159. This same general structure is shared by complexes of tartaric acid with Sb(III), As(III), Cu(II), and Cr(III) [; and references cited therein.
    • (1976) Inorg. Chem. , vol.15 , pp. 154-159
    • Robbins, G.L.1    Tapscott, R.E.2
  • 175
    • 36849106818 scopus 로고
    • The preferred ground state conformation of allyl alcohol itself appears to be the gauche rotamer, in which the allylic C-O bond is nearly coplanar with the olefin π system: a. Microwave spectrum:
    • Murty A.N., Curl R.F. J. Chem. Phys. 1967, 46:4176-4180. The preferred ground state conformation of allyl alcohol itself appears to be the gauche rotamer, in which the allylic C-O bond is nearly coplanar with the olefin π system: a. Microwave spectrum:.
    • (1967) J. Chem. Phys. , vol.46 , pp. 4176-4180
    • Murty, A.N.1    Curl, R.F.2
  • 178
    • 0242454670 scopus 로고
    • d. Ab initio calculation in which the cis conformation is slightly favored:
    • Grunde R., Azman A. J. Mol. Struct. 1975, 27:212-215. d. Ab initio calculation in which the cis conformation is slightly favored:.
    • (1975) J. Mol. Struct. , vol.27 , pp. 212-215
    • Grunde, R.1    Azman, A.2
  • 181
    • 85080382100 scopus 로고    scopus 로고
    • When the allyl alcohol epoxidation reaction mixture is treated with the effective nucleophile thiophenol (PhSH) in the presence of added Ti(OiPr)4
    • unpublished results, the epoxy alcohol is opened in situ to give 3-thiophenoxy-1,2-propanediol in 88% yield and 89% ee.
    • d. Ko, S.-Y., Hollinshead, D. M., and Sharpless, K. B., unpublished results. When the allyl alcohol epoxidation reaction mixture is treated with the effective nucleophile thiophenol (PhSH) in the presence of added Ti(OiPr)4, the epoxy alcohol is opened in situ to give 3-thiophenoxy-1,2-propanediol in 88% yield and 89% ee.
    • Ko, S.-Y.1    Hollinshead, D.M.2    Sharpless, K.B.3
  • 186
    • 0003649034 scopus 로고
    • Springer-Verlag, Vienna, The carbonyl groups of amides are significantly more basic than those of esters. See: (1977). Chemtech
    • Gutmann V. "Coordination Chemistry in Non-aqueous Solutions," 1968, 19. Springer-Verlag, Vienna, The carbonyl groups of amides are significantly more basic than those of esters. See: (1977). Chemtech pp. 255-263.
    • (1968) "Coordination Chemistry in Non-aqueous Solutions," , pp. 19+255-263
    • Gutmann, V.1
  • 195
    • 0002422122 scopus 로고
    • 3 in solution has two five-coordinate titanium centers in each trimer unit [
    • 3 in solution has two five-coordinate titanium centers in each trimer unit [.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 1521-1526
    • Russo, W.R.1    Nelson, W.H.2
  • 199
    • 0000911879 scopus 로고
    • 4, complexes of acetylacetonate, quinolinate, oxalate, and similar ligands, and in diolate complexes. See ref. 71a,b. On exception to octahedral coordination is the six-coordinate peroxotitanium porphyrins [
    • 4, complexes of acetylacetonate, quinolinate, oxalate, and similar ligands, and in diolate complexes. See ref. 71a,b. On exception to octahedral coordination is the six-coordinate peroxotitanium porphyrins [.
    • (1978) Inorg. Chem. , vol.17 , pp. 1228-1237
    • Guilard, R.1    Latour, J.-M.2    Lecomte, C.3    Marchan, J.-C.4    Protas, J.5    Ripoll, D.6
  • 200
    • 84944175278 scopus 로고
    • Seven-coordinate. Many Ti(IV)-peroxo complexes are seven coordinate
    • Schwarzenbach D. Helv. Chim. Acta 1977, 55:2990-3004. d. Seven-coordinate. Many Ti(IV)-peroxo complexes are seven coordinate.
    • (1977) Helv. Chim. Acta , vol.55 , pp. 2990-3004
    • Schwarzenbach, D.1
  • 201
    • 85080394319 scopus 로고
    • Inorg. Chem. 1969, 9:2391-2397.
    • (1969) Inorg. Chem. , vol.9 , pp. 2391-2397


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.