104208-01-7Relevant academic research and scientific papers
Syntheses of (5E)-PGE2 and New 6-Functionalized Derivatives by the Use of Palladium-Catalyzed Decarboxylative Allylic Alkylation
Tanaka, Toshio,Okamura, Noriaki,Bannai, Kiyoshi,Hazato, Atsuo,Sugiura, Satoshi,et al.
, p. 6747 - 6758 (1986)
(5E)-Prostaglandin E2 (7) was synthesized form (R)-4-t-butyldimethylsilyloxy-2-cyclopentenone (1) by in situ 2-alkenyloxycarbonylation of the organocopper conjugate-addition adduct (3) followed by intramolecular palladium-catalyzed decarboxylative allylic alkylation.The (5E)-prostaglandin E2 skeleton was also obtained from the β-keto allylic ester (11) by a similar decarboxylative allylic alkylation.The decarboxylative allylic alkylation of another type of the three-component coupling product (12) gave new 6-methyleneprostaglandin E1 skeleton (15a), which was converted into new 6-methylprostaglandin I methyl ester (20) via 6-methyleneprostaglandin F1α derivative (16) by two different ways.The stereochemistry of this intramolecular decarboxylative allylic alkylation was discussed in the reaction of 2-cyclopentanone systems.
On the reactivity of imidazole carbamates and ureas and their use as esterification and amidation reagents
Heller, Stephen T.,Sarpong, Richmond
body text, p. 8851 - 8859 (2011/12/02)
The optimization, substrate scope, and mechanism of esterification and amidation of carboxylic acids mediated by imidazole-based reagents are discussed. The innate reactivity of carbonylimidazole reagents with a range of nucleophiles is also explored. New reagents developed for the synthesis of α,β-unsaturated esters are described, as are reagents for the preparation of tertiary amides directly from carboxylic acids.
Chemoselective esterification and amidation of carboxylic acids with imidazole carbamates and ureas
Heller, Stephen T.,Sarpong, Richmond
supporting information; experimental part, p. 4572 - 4575 (2010/12/25)
Imidazole carbamates and ureas were found to be chemoselective esterification and amidation reagents. A wide variety of carboxylic acids were converted to their ester or amide analogues by a simple synthetic procedure in high yields.
The O-acylation of ketone enolates by allyl 1H-imidazole-1-carboxylate mediated with boron trifluoride etherate - A convenient procedure for the synthesis of substituted allyl enol carbonates
Trost, Barry M.,Xu, Jiayi
, p. 9372 - 9375 (2008/03/13)
(Chemical Equation Presented) A convenient access to substituted allyl enol carbonates was established through the reaction of ketone enolates with the complex of allyl 1H-imidazole-1-carboxylates and boron trifluoride etherate.
