Catalytic asymmetric aza-Michael-Michael addition cascade: enantioselective synthesis of polysubstituted 4-aminobenzopyrans.
A catalytic asymmetric aza-Michael-Michael addition cascade of anilines to nitroolefin enoates in the presence of chiral bifunctional thiourea catalysts has been disclosed. This reaction provides a mild and efficient approach to polysubstituted chiral 4-aminobenzopyrans bearing three consecutive stereocenters in high yields with excellent stereoselectivities.
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China.
Xu-Fan
XF
Wang
Jing
J
An
Xiao-Xiao
XX
Zhang
Fen
F
Tan
Jia-Rong
JR
Chen
Wen-Jing
WJ
Xiao
D000475:Alkenes / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
D000475:Alkenes; D000814:Aniline Compounds; D001578:Benzopyrans; D009574:Nitro Compounds; D013890:Thiourea