Heterocyclic Compounds
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ChemInform Abstract: Conjugate Hydroboration-Reduction and Organolithium Additions to Acylketene Acetals. Synthesis of Monoprotected β-Dicarbonyls.
First published: September 11, 1990
Abstract
The 2-(acylmethylene)-1,3-dioxolanes (IV) and (VI) are prepared from the ketones (I) or (V) via consecutive reaction with dimethyl carbonate (II) and 2-chloroethanol (III), followed by base-induced ring closure.
ChemInform Abstract
The 2-(acylmethylene)-1,3-dioxolanes (IV) and (VI) are prepared from the ketones (I) or (V) via consecutive reaction with dimethyl carbonate (II) and 2-chloroethanol (III), followed by base-induced ring closure. (IV) is treated with the borane THF complex (VII) and then hydrolyzed to yield the β-keto aldehyde acetal (IX). Alkylation of (IV) or (VI) with the organolithiums (X) or (XIII) produces the 1,3-diketone monoacetals (XII), (XIV), or (XV).
