Diastereoselective syntheses of functionalized five-membered carbocycles and heterocycles by a SmI2-promoted intramolecular coupling of bromoalkynes and alpha,beta-unsaturated esters.
An intramolecular coupling of bromoalkynes with alpha,beta-unsaturated esters afforded functionalized five-membered carbocycles and heterocycles with high diastereoselectivities in excellent yields. The vinyl bromides newly generated as the products serve as adequate intermediates for further chemical modification.
Takahashi
Kazunori
K
Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan.
Honda
Toshio
T
D000480:Alkynes / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000480:Alkynes; D004952:Esters; D006571:Heterocyclic Compounds; D006842:Hydrocarbons, Brominated; D006844:Hydrocarbons, Cyclic