Y. Tamaru, M. Hojo, Z. Yoshida
Feb 1, 1991
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Influential Citations
90
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Journal
Journal of Organic Chemistry
Abstract
Palladium(II)-catalyzed dicarbonylation of 3-buten-1-ols (1) in the presence of propylene oxide and ethyl orthoacetate in methanol-dichloromethane under carbon monoxide at atmospheric pressure afforded α-[(methoxycarbonyl)methyl]-γ-butyrolactones (2) in good yields. This dicarbonylation reaction occurs via stereospecific cis addition. Under similar conditions, 4-(trimethylsilyl)-3-butyn-1-ols (4a and 4b) undergo dicarbonylation to provide cis-dicarbonylated α-methylene-γ-butyrolactones (5a and 5b, respectively). 4-Alkyl- and 4-aryl-3-butyn-1-ols (4c-g), on the other hand, undergo trans alkoxycarbonylation across the triple bond and selectively furnish E tetrasubstituted α-methylene-γ-butyrolactones (6)