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Chemoselectivity in Reactions of Organotitanium Reagents with Carbonyl Compounds

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Organotitanium Reagents in Organic Synthesis

Part of the book series: Reactivity and Structure: Concepts in Organic Chemistry ((REACTIVITY,volume 24))

Abstract

Grignard and alkyllithium compounds as well as a host of resonance stabilized and hetero-atom substituted carbanions add smoothly to carbonyl compounds. Unfortunately, in case of molecules with several functional groups, these C—C bond forming reactions are of little value due to the lack of chemoselectivity (Chapter 1). For example, the keto-aldehyde 1 reacts with the lithium enolate 2 derived from ethyl acetate to provide a ~1:1:1 mixture of aldol adducts 3, 4, and 5 in addition to some starting material 1 [1,2].

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  1. Fachbereich Chemie der Universität Marburg, D-3550, Marburg, Germany

    Professor Dr. Manfred T. Reetz

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  1. Professor Dr. Manfred T. Reetz
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Reetz, M.T. (1986). Chemoselectivity in Reactions of Organotitanium Reagents with Carbonyl Compounds. In: Organotitanium Reagents in Organic Synthesis. Reactivity and Structure: Concepts in Organic Chemistry, vol 24. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-70704-9_3

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  • DOI: https://doi.org/10.1007/978-3-642-70704-9_3

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