Highly efficient and generalized asymmetric synthesis of quaternary stereogenic carbon-containing β-amino indanones/indanoles via Mannich-type additions between 1-indanones and N-tert-butanesulfinylketimines.
Here we report that, unlike other ketones, 1-indanone and acetophenone derived enolates undergo Mannich-type addition reactions with N-tert-butanesulfinyl ketimines with excellent yields (up to 98%) and diastereoselectivity (>99/1). The resulting compounds represent a new type of biologically relevant β-aminoketone derivative bearing quaternary stereogenic carbon, which could be further converted into the corresponding β-amino ketones and β-amino alcohols, possessing three consecutive stereogenic centres.
School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China. hanjl@nju.edu.cn.
Lingmin
L
Wu
Chen
C
Xie
Haibo
H
Mei
Vadim A
VA
Soloshonok
Jianlin
J
Han
Yi
Y
Pan
D000098:Acetophenones / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D007189:Indans / Q000138:chemical synthesis* / Q000737:chemistry; D008352:Mannich Bases / Q000737:chemistry*; D008968:Molecular Conformation; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D066244:Proton Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
D000098:Acetophenones; D007097:Imines; D007189:Indans; D008352:Mannich Bases; D009570:Nitriles; C542835:ketimine; D002244:Carbon; C038699:acetophenone