Boronate urea activation of nitrocyclopropane carboxylates.
Boronate ureas operate as catalysts for the activation of nitrocyclopropane carboxylates in nucleophilic ring-opening reactions. A variety of amines were found to open the urea-activated nitrocyclopropane carboxylates, generating highly useful nitro ester building blocks in good yields. Standard manipulations allow access to a wide range of valuable compounds from the ring-opened products with direct applications in bioactive target synthesis.
Department of Chemistry, The Ohio State University, 100 W. 18th Avenue, Columbus, Ohio 43210, USA.
Sonia S
SS
So
Tyler J
TJ
Auvil
Victoria J
VJ
Garza
Anita E
AE
Mattson
D001897:Boronic Acids / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014508:Urea / Q000737:chemistry*
D001897:Boronic Acids; D002264:Carboxylic Acids; D003521:Cyclopropanes; D009574:Nitro Compounds; D014508:Urea; C030797:cyclopropane