Realization of anti-SN2' selective allylation of 4-cyclopentene-1,3-diol monoester with aryl- and alkenyl-zinc reagents.
Anti-SN2' mode of allylation of the monoester of 4-cyclopentene-1,3-diol with aryl and alkenyl anions was achieved, for the first time, with the MeOCH2CO2- group as a leaving group to which R-ZnBr and CuCl (as a catalyst) were best fitted. The aryl groups successfully installed were Ph, o- and p-MeC6H4, o-MOMOC6H4, o-MeOC6H4, and p-F-C6H4, while cis and trans alkenyl groups were attached with retention of the olefinic stereochemistries.
Nakata
Kenya
K
Department of Biomolecular Engineering, Tokyo Institute of Technology, Box B52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan.
Kiyotsuka
Yohei
Y
Kitazume
Tomoya
T
Kobayashi
Yuichi
Y
D000475:Alkenes / Q000737:chemistry*; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
D000475:Alkenes; D003517:Cyclopentanes; D007202:Indicators and Reagents; D015032:Zinc