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85163235486
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Although the stereogenic center is not involved in the substitution of the alcoholates in 3d and 3e for the acetoxy group in 2 its designation changes. That is because the reaction of the (S)-glycerol 3d gives the (2R)-2,3-dihydroxypropyloxycarbene complex 4d. This is due to a change in the priority of the different groups at the stereogenic center.
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3 > CO > C(OR*)Ph. - [9a] C. Lecomte, Y. Dusausoy. J. Protas, J. Tirouflet, A. Dormond. J. Organomet. Chem. 1974, 73, 67-76. [9b] T. E. Sloan, Top. Stereochem. 1981, 72, 1-36.
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For hindered rotation around the C(carbene)-OR bond see e.g.: [14a] C. G. Kreiter, E. O.Fischer, Angew. Chem 1969, 81, 780-781; Angew. Chem. Int. Ed. Engl. 1969, 8, 761. [14b] E. O. Fischer, C. G. Kreiter, H. J. Kollmeier, J. Müller, R. D. Fischer, J. Organomet Chem. 1971, 28, 237-258. [14c] E. O. Fischer, H.-J. Beck, C. G. Kreiter, J. Lynch, J. Müller, E. Winkler, Chem. Ber. 1972, 105, 162-172. [14d] V. Guerchais, C. Lapinte, J.-Y Thépot, L. Toupet, Organometallics 1988, 7, 604-612.
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Kreiter, C.G.1
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84981000917
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For hindered rotation around the C(carbene)-OR bond see e.g.: [14a] C. G. Kreiter, E. O.Fischer, Angew. Chem 1969, 81, 780-781; Angew. Chem. Int. Ed. Engl. 1969, 8, 761. [14b] E. O. Fischer, C. G. Kreiter, H. J. Kollmeier, J. Müller, R. D. Fischer, J. Organomet Chem. 1971, 28, 237-258. [14c] E. O. Fischer, H.-J. Beck, C. G. Kreiter, J. Lynch, J. Müller, E. Winkler, Chem. Ber. 1972, 105, 162-172. [14d] V. Guerchais, C. Lapinte, J.-Y Thépot, L. Toupet, Organometallics 1988, 7, 604-612.
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35
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0001189336
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For hindered rotation around the C(carbene)-OR bond see e.g.: [14a] C. G. Kreiter, E. O.Fischer, Angew. Chem 1969, 81, 780-781; Angew. Chem. Int. Ed. Engl. 1969, 8, 761. [14b] E. O. Fischer, C. G. Kreiter, H. J. Kollmeier, J. Müller, R. D. Fischer, J. Organomet Chem. 1971, 28, 237-258. [14c] E. O. Fischer, H.-J. Beck, C. G. Kreiter, J. Lynch, J. Müller, E. Winkler, Chem. Ber. 1972, 105, 162-172. [14d] V. Guerchais, C. Lapinte, J.-Y Thépot, L. Toupet, Organometallics 1988, 7, 604-612.
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Fischer, E.O.1
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Kollmeier, H.J.3
Müller, J.4
Fischer, R.D.5
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36
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84984226189
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For hindered rotation around the C(carbene)-OR bond see e.g.: [14a] C. G. Kreiter, E. O.Fischer, Angew. Chem 1969, 81, 780-781; Angew. Chem. Int. Ed. Engl. 1969, 8, 761. [14b] E. O. Fischer, C. G. Kreiter, H. J. Kollmeier, J. Müller, R. D. Fischer, J. Organomet Chem. 1971, 28, 237-258. [14c] E. O. Fischer, H.-J. Beck, C. G. Kreiter, J. Lynch, J. Müller, E. Winkler, Chem. Ber. 1972, 105, 162-172. [14d] V. Guerchais, C. Lapinte, J.-Y Thépot, L. Toupet, Organometallics 1988, 7, 604-612.
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Fischer, E.O.1
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Lynch, J.4
Müller, J.5
Winkler, E.6
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37
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0001722358
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-
For hindered rotation around the C(carbene)-OR bond see e.g.: [14a] C. G. Kreiter, E. O.Fischer, Angew. Chem 1969, 81, 780-781; Angew. Chem. Int. Ed. Engl. 1969, 8, 761. [14b] E. O. Fischer, C. G. Kreiter, H. J. Kollmeier, J. Müller, R. D. Fischer, J. Organomet Chem. 1971, 28, 237-258. [14c] E. O. Fischer, H.-J. Beck, C. G. Kreiter, J. Lynch, J. Müller, E. Winkler, Chem. Ber. 1972, 105, 162-172. [14d] V. Guerchais, C. Lapinte, J.-Y Thépot, L. Toupet, Organometallics 1988, 7, 604-612.
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Guerchais, V.1
Lapinte, C.2
Thépot, J.-Y.3
Toupet, L.4
-
48
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85163226436
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note
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Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road. Cambridge CB2 1EZ, UK [fax: int. code +44(1223)336-033, e-mail: deposit@ccdc.cam.ac.uk].
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