Organocatalytic asymmetric Friedel-Crafts alkylation/cascade reactions of naphthols and nitroolefins.
The asymmetric Michael-type Friedel-Crafts reaction of naphthols and nitroolefins promoted by bifunctional thiourea-tertiary amine organocatalysts (up to 95% ee) was investigated; on simply extending the reaction time further cascade reactions could occur to generate enantiopure dimeric tricyclic 1,2-dihydronaphtho[2,1-b]furanyl-2-hydroxylamine derivatives.
Liu
Tian-Yu
TY
Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Cui
Hai-Lei
HL
Chai
Qian
Q
Long
Jun
J
Li
Bang-Jing
BJ
Wu
Yong
Y
Ding
Li-Sheng
LS
Chen
Ying-Chun
YC
D000475:Alkenes / Q000737:chemistry*; D000478:Alkylation; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D019281:Dimerization; D005663:Furans / Q000737:chemistry; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis; D006898:Hydroxylamines / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry; D009284:Naphthols / Q000737:chemistry*; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry
D000475:Alkenes; D000588:Amines; D005663:Furans; D006844:Hydrocarbons, Cyclic; D006898:Hydroxylamines; D009281:Naphthalenes; D009284:Naphthols; D009574:Nitro Compounds; C086079:1,2-dihydronaphthalene; D013890:Thiourea