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.
Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan.
Kazunori
K
Takahashi
Toshio
T
Honda
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