Highly efficient route to functionalized tetrahydrocarbazoles using a tandem cross-metathesis/intramolecular-hydroarylation sequence.
The scope of the novel ruthenium-catalyzed tandem cross-metathesis/intramolecular-hydroarylation sequence is described. This methodology offers a practical and efficient synthesis of structurally diverse and complex tetrahydrocarbazoles in good to excellent yields (up to 98%). Moreover, preliminary efforts towards the development of an enantioselective version of the current process by sequential catalysis with ruthenium complex and chiral amine are presented, with high yields and enantioselectivities (up to 88% yield and 91% ee).
An
Xiao-Lei
XL
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China.
Chen
Jia-Rong
JR
Li
Chang-Feng
CF
Zhang
Fu-Gen
FG
Zou
You-Quan
YQ
Guo
Ying-Cen
YC
Xiao
Wen-Jing
WJ
D000588:Amines / Q000737:chemistry; D002227:Carbazoles / Q000737:chemistry*; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
D000588:Amines; D002227:Carbazoles; D056831:Coordination Complexes; D006571:Heterocyclic Compounds; D012428:Ruthenium