title: One-Carbon Homologation of Primary Alcohols to Carboxylic Acids, Esters, and Amides via Mitsunobu Reactions with MAC Reagents.
abstract: A method is reported for the one-carbon homologation of an alcohol to the extended carboxylic acid, ester, or amide. The process involves the Mitsunobu reaction with an alkoxymalononitrile, followed by unmasking in the presence of a suitable nucleophile. The homologation and unmasking can even be performed in a one-pot process in high yield.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University , 1-8-1 Inohana, Chiba 260-8675, Japan.|Center for Environment, Health and Field Sciences, Chiba University , 6-2-1 Kashiwa-no-ha, Kashiwa 277-0882, Japan.
authors.forename: Natsuko
authors.initials: N
authors.lastname: Kagawa
authors.affiliation: Department of Chemistry, University of Chicago , 5735 South Ellis Avenue, Chicago, Illinois 60637, United States.
authors.forename: Antoinette E
authors.initials: AE
authors.lastname: Nibbs
authors.affiliation: Department of Chemistry, University of Chicago , 5735 South Ellis Avenue, Chicago, Illinois 60637, United States.
authors.forename: Viresh H
authors.initials: VH
authors.lastname: Rawal
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000577:Amides; D002264:Carboxylic Acids; D004952:Esters; D007202:Indicators and Reagents; D002244:Carbon