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Volumn 116, Issue 19, 1994, Pages 8470-8478

Toward an Understanding of the High Enantioselectivity in the Osmium-Catalyzed Asymmetric Dihydroxylation. 2. A Qualitative Molecular Mechanics Approach

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EID: 0000770498     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00098a006     Document Type: Article
Times cited : (119)

References (51)
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    • Catalytic Asymmetric Dihydroxylation in Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim
    • Johnson, R. A.; Sharpless, K. B. Catalytic Asymmetric Dihydroxylation in Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993; pp 227-272.
    • (1993) , pp. 227-272
    • Johnson, R.A.1    Sharpless, K.B.2
  • 15
    • 0040485959 scopus 로고
    • [2 + 2] cycloaddition reactions to form metallacyclobutane complexes can be very fast and reversible; for a review, see:
    • J⊘rgensen, K. A.; Schictt, B. Chem. Rev. 1990, 90, 1483-1506. [2 + 2] cycloaddition reactions to form metallacyclobutane complexes can be very fast and reversible; for a review, see:
    • (1990) Chem. Rev. , vol.90 , pp. 1483-1506
    • J⊘rgensen, K.A.1    Schictt, B.2
  • 16
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    • Recently, a chromaoxetane was synthesised and characterized, see:
    • Feldman, J.; Schrock, R. R. Prog. Inorg. Chem. 1991, 39, 1. Recently, a chromaoxetane was synthesised and characterized, see:
    • (1991) Prog. Inorg. Chem. , vol.39 , pp. 1
    • Feldman, J.1    Schrock, R.R.2
  • 19
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    • The same nonlinear temperature behavior has recently been observed in chemoselectivity studies: McGrath, D. V.; Makita, A.; Sharpless, K. B., manuscript in preparation.
    • Göbel, T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1993, 32, 1329. The same nonlinear temperature behavior has recently been observed in chemoselectivity studies: McGrath, D. V.; Makita, A.; Sharpless, K. B., manuscript in preparation.
    • (1993) Angew. Chem., Int. Ed. Engl. , vol.32 , pp. 1329
    • Göbel, T.1    Sharpless, K.B.2
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    • Ph.D. Thesis, Massachusetts Institute of Technology
    • Kwong, H.-L. Ph.D. Thesis, Massachusetts Institute of Technology, 1993.
    • (1993)
    • Kwong, H.-L.1
  • 23
    • 0014119018 scopus 로고
    • An alternative pathway has been reported to be second order in ligand, yielding osmate esters with two coordinated ligands as the end product, in the presence of ammonia or pyridine, see:
    • An alternative pathway has been reported to be second order in ligand, yielding osmate esters with two coordinated ligands as the end product, in the presence of ammonia or pyridine, see: Burton, K. Biochem. J. 1967, 104, 686.
    • (1967) Biochem. J. , vol.104 , pp. 686
    • Burton, K.1
  • 31
    • 85022487187 scopus 로고    scopus 로고
    • We have not been able to observe an osmaoxetane intermediate in a photochemically induced osmylation reaction using matrix isolation techniques: unpublished results.
    • We have not been able to observe an osmaoxetane intermediate in a photochemically induced osmylation reaction using matrix isolation techniques: McGrath, D. V.; Brabson, G. D.; Andrews, L.; Sharpless, K. B., unpublished results.
    • McGrath, D.V.1    Brabson, G.D.2    Andrews, L.3    Sharpless, K.B.4
  • 33
    • 0000876807 scopus 로고
    • Further X-ray structures obtained in our group were used in the preliminary work: Kolb, H. C.; McGrath, D. V.: Sharpless, K. B., unpublished data.
    • Svendsen, J. S.; Markó, I.; Jacobsen, E. N.; Rao, C. P.; Bott, S.; Sharpless, K. B. J. Org. Chem. 1989, 54, 2263. Further X-ray structures obtained in our group were used in the preliminary work: Kolb, H. C.; McGrath, D. V.: Sharpless, K. B., unpublished data.
    • (1989) J. Org. Chem. , vol.54 , pp. 2263
    • Svendsen, J.S.1    Markó, I.2    Jacobsen, E.N.3    Rao, C.P.4    Bott, S.5    Sharpless, K.B.6
  • 37
    • 85022475020 scopus 로고    scopus 로고
    • Constraining this bond to a shorter distance will have very little effect on the calculated energies of optimized structures: unpublished data.
    • Constraining this bond to a shorter distance will have very little effect on the calculated energies of optimized structures: Kolb, H. C.; Norrby, P.-O.; Becker, H.; Sharpless, K. B., unpublished data.
    • Kolb, H.C.1    Norrby, P.-O.2    Becker, H.3    Sharpless, K.B.4
  • 45
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    • The hydrogen is believed to be too hard in MM2 and has been adjusted in the more recent MM3:
    • The hydrogen is believed to be too hard in MM2 and has been adjusted in the more recent MM3: Allinger, N. L.; Yuh, Y. H.; Lii, J.-H. J. Am. Chem. Soc. 1989, 111, 8551.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8551
    • Allinger, N.L.1    Yuh, Y.H.2    Lii, J.-H.3
  • 46
    • 0001227655 scopus 로고
    • Offset parallel interactions between aromatic systems can be attractive and they become more favorable with increasing size of the arene. For a model which explains the geometric requirements for interactions between aromatic systems, see: See also:
    • Offset parallel interactions between aromatic systems can be attractive and they become more favorable with increasing size of the arene. For a model which explains the geometric requirements for interactions between aromatic systems, see: Hunter, C. A.; Sanders, J. K. M., J. Am. Chem. Soc. 1990, 112, 5525. See also:
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 5525
    • Hunter, C.A.1    Sanders, J.K.M.2
  • 50
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    • Recent investigations show thai both the enantioselectivities and rate constants drop on increasing the size of the substiluents of 3,5-disubstituted styrenes, probably because large substiluents disfavor the stacked arrangement shown in Figure 6; in press.
    • Recent investigations show thai both the enantioselectivities and rate constants drop on increasing the size of the substiluents of 3,5-disubstituted styrenes, probably because large substiluents disfavor the stacked arrangement shown in Figure 6; Becker, H.; Ho, P.T.; Kolb, H.; Loren. S.; Norrby, P.-O.; Sharpless, K. B. Tetrahedron Lett., in press.
    • Tetrahedron Lett.
    • Becker, H.1    Ho, P.T.2    Kolb, H.3    Loren, S.4    Norrby, P.-O.5    Sharpless, K.B.6


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