A novel stereocontrolled synthesis of 1,2-trans cyclopropyl ketones via suzuki-type coupling of acid chlorides with cyclopropylboronic acids.
[reaction: see text] The palladium-catalyzed cross-coupling reaction of cyclopropylboronic acids with acyl chlorides was achieved by the combination of Ag(2)O and K(2)CO(3) as the base. Highly enantiomerically enriched cyclopropyl ketones (ee >90%) were also obtained by the reaction of corresponding chiral cyclopropylboronic acids.
Chen
H
H
Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Academia Sinica, China.
Deng
M Z
MZ
D001897:Boronic Acids / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry; D003521:Cyclopropanes / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis*; D010165:Palladium
D001897:Boronic Acids; D002264:Carboxylic Acids; D003432:Cross-Linking Reagents; D003521:Cyclopropanes; D007659:Ketones; D010165:Palladium