Rearrangements of organometallic compounds : XVII. Synthesis of lactones via the titanium-catalyzed hydromagnesiation of alkenols |
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Authors: | John J Eisch James E Galle |
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Institution: | Department of Chemistry, State University of New York at Binghamton, Binghamton, New York 13901 U.S.A. |
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Abstract: | An efficient, two-step synthesis is presented for preparing γ- and δ-lactones from aldehydes or ketones. (1) the addition of vinyl- or allyl-Grignard reagents to the appropriate carbonyl substrate; and (2) the titanium-catalyzed hydromagnesiation of the resulting alkenols with ethyl Grignard reagent and (η5-C5H5)2TiCl2, followed by carbonation. The selectivity of hydrometallation observed with 3-butenyl(methyl)vinylcarbinol indicates the importance of alkoxytitanium hydrides in determining the course of reaction. |
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