title: Unusual reaction behavior of gem-difluorocyclopropane derivatives: stereoselective synthesis of β-monofluoroallylic alcohols, ethers, esters, and amide.
abstract: On treating gem-difluorocyclopropylstannanes, derived from the radical hydrostannation of gem-difluorocyclopropenes, with 1.5 equiv of MeLi in THF at -78 °C for 5 min, followed by quenching the reaction with various agents, such as H2O, alcohols, carboxylic acids, and tosylamide, the corresponding β-fluoroallylic alcohols, ethers, esters, and amide were obtained with exclusive Z-selectivity in acceptable yields.
authors: Department of Chemistry and Materials Technology, Kyoto Institute of Technology , Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan.
authors: Takashi
authors: T
authors: Nihei
authors: Tomoko
authors: T
authors: Hoshino
authors: Tsutomu
authors: T
authors: Konno
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D002264:Carboxylic Acids; D003521:Cyclopropanes / Q000737:chemistry*; D004952:Esters; D004987:Ethers / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000577:Amides; D002264:Carboxylic Acids; D003521:Cyclopropanes; D004952:Esters; D004987:Ethers; D006845:Hydrocarbons, Fluorinated