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.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, PR China.
Ke-Jia
KJ
Wu
Gong-Qiang
GQ
Li
Yi
Y
Li
Li-Xin
LX
Dai
Shu-Li
SL
You
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