Asymmetric synthesis of 3-substituted isoindolinones: application to the total synthesis of (+)-lennoxamine.
An anionic chiral auxiliary mediated asymmetric alkylation of carbamate 2 provides 3-substituted isoindolinones 4 in high ee. This methodology was used in the first asymmetric synthesis of (+)-lennoxamine.
Comins
Daniel L
DL
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA. daniel_comins@nscu.edu
Schilling
Stefan
S
Zhang
Yanchen
Y
D018360:Crystallography, X-Ray; D004146:Dioxanes / Q000138:chemical synthesis*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007211:Indoles / Q000138:chemical synthesis*; D008958:Models, Molecular; D013237:Stereoisomerism
D004146:Dioxanes; D006571:Heterocyclic Compounds; D007211:Indoles; C442893:lennoxamine