N-heterocyclic carbene-catalyzed homoenolate additions with N-aryl ketimines as electrophiles: efficient synthesis of spirocyclic γ-lactam oxindoles.
In pole position: A simple and efficient approach to spirocyclic γ-lactam oxindoles by the N-heterocyclic carbene catalyzed addition of homoenloate equivalents to N-aryl isatinimines has been developed (see scheme). The use of N-aryl isatinimines as electrophiles in the NHC-catalyzed umpolung reaction of α,β-unsaturated aldehydes is demonstrated for the first time.
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, PR China.
Bo
B
Zhang
Peng
P
Feng
Li-Hui
LH
Sun
Yuxin
Y
Cui
Song
S
Ye
Ning
N
Jiao
D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D006571:Heterocyclic Compounds; D007097:Imines; D007211:Indoles; D007769:Lactams; D009570:Nitriles; D000078183:Oxindoles; D013141:Spiro Compounds; C542835:ketimine; C022960:2-oxindole; C030011:carbene; D008697:Methane