N-heterocyclic carbene-catalyzed tandem aza-benzoin/Michael reactions: on site reversal of the reactivity of N-Boc imines.
A tandem NHC-catalyzed aza-benzoin/Michael reaction has been developed as a method to efficiently produce dihydroindenones and pyrrolidinone-containing tricycles. The novel reaction pattern involves tert-butyl aryl(tosyl)methylcarbamates reacting as both electrophile and nucleophile on the same carbon.
Wu
Ke-Jia
KJ
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, PR China.
Li
Gong-Qiang
GQ
Li
Yi
Y
Dai
Li-Xin
LX
You
Shu-Li
SL
D001372:Aza Compounds / Q000737:chemistry*; D001573:Benzoin / Q000737:chemistry*; D001665:Binding Sites; D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007192:Indenes / Q000138:chemical synthesis / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D011760:Pyrrolidinones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D001372:Aza Compounds; D006571:Heterocyclic Compounds; D007097:Imines; D007192:Indenes; D011760:Pyrrolidinones; C030011:carbene; D001573:Benzoin; D008697:Methane