Stereochemical control in reactions of chiral ketone with 2-lithiated substituted ferrocene derivatives |
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| Authors: | Troitskaya L. L. Demeshchik T. V. Ovseenko S. T. Starikova Z. A. Sokolov V. I. Malezieux B. Gruselle M. |
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| Affiliation: | (1) A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russian Federation;(2) Laboratory of Inorganic Chemistry and Molecular Materials, P. and M. Curie University, National Center for Scientific Research Unit, 7071, France, 4 pl. Jussieu, 75252 Paris, Bat. 42 |
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| Abstract: | The formation of a new chiral center in the reactions of ketone 4-MeOC6H4CH(Et)C(O)Et with planar-chiral 2-lithio-1-methyl- and 1-chloro-2-lithioferrocenes proceeded stereoselectively to give two diastereomers in a ratio of  3 : 2 or a single diastereomer, respectively, out of four possible diastereomeric 4-aryl-3-ferrocenylhexan-3-ols. The replacement of the hydroxy group in the resulting compounds by hydrogen under the conditions of ionic hydrogenation was studied. The configurations of the reaction products were established by X-ray diffraction analysis and 1H NMR spectroscopy. |
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| Keywords: | lithioferrocenes planar and central chirality 1,2-addition at the CO group stereochemical control |
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