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This type of alkylation is exemplified by the Lewis acid promoted addition of allylic silanes and stannanes to carbonyl compounds. See: (a) Colvin, E. W. Silicon in Organic Synthesis; Butterworths: London, 1981; p 97. (b) Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1982, 21, 555. (c) Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: New York, 1983; p 173.
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For equatorial selectivity with silyl hydride, see
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Conjugate addition of lithium (E)-1-alkenyltrialkylaluminate to cyclopentenones has been developed in prostaglandin synthesis with limited synthetic utility in view of several side reactions including the undesired alkyl transfer, conjugate reduction, and anionic oligomerization of cyclopentenones Floyd, M. B.; Weiss, M. J. Prostaglandins 1973, 3, 921. Bernady, K. F.; Poletto, J. F.; Weiss, M. J. Tetrahedron Lett. 1975, 765. Floyd, M. B.; Weiss, M. J. J. Org. Chem. 1979, 44, 71. Bernady, K. F.; Floyd, M. B.; Poletto, J. F.; Weiss, M. J. J. Am. Chem. Soc. 1979, 44, 1438. The Ni(acac)2 catalyzed conjugate methylation of enones by lithium tetramethylaluminate has been also reported; Ashby, E. C.; Heinsohn, G. J. Org. Chem. 1974, 39, 3297
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