Enantioselective trapping of an α-chiral carbanion of acyclic nitrile by a carbon electrophile.
An α-chiral nitrile carbanion generated by deprotonation of enantioenriched O-carbamoyl cyanohydrin was trapped in situ with ethyl cyanoformate to give the corresponding ester derivative in 92% yield and 90 : 10 er, providing the first example of trapping of an α-chiral acyclic nitrile carbanion that has been considered to be very configurationally labile.
Department of Synthetic Organic Chemistry, Graduate School of Biomedical Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-Ku, Hiroshima, 734-8553, Japan.
Michiko
M
Sasaki
Tomo
T
Takegawa
Hidaka
H
Ikemoto
Masatoshi
M
Kawahata
Kentaro
K
Yamaguchi
Kei
K
Takeda
D000838:Anions / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
D000838:Anions; D009570:Nitriles; D012997:Solvents; C430593:cyanohydrin; D002244:Carbon