Article

Realization of anti-SN2' selective allylation of 4-cyclopentene-1,3-diol monoester with aryl- and alkenyl-zinc reagents.

Department of Biomolecular Engineering, Tokyo Institute of Technology, Box B52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan.
Organic Letters (impact factor: 5.86). 05/2008; 10(7):1345-8. DOI:10.1021/ol8002354 pp.1345-8
Source: PubMed

ABSTRACT 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.

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Keywords

alkenyl anions
 
Anti-SN2' mode
 
cis
 
MeOCH2CO2- group
 
monoester
 
p-MeC6H4
 
R-ZnBr
 
retention
 
trans alkenyl groups
 

Kenya Nakata