Chemical Communications 2007-06-14

Organocatalytic asymmetric Friedel-Crafts alkylation/cascade reactions of naphthols and nitroolefins.

Tian-Yu Liu, Hai-Lei Cui, Qian Chai, Jun Long, Bang-Jing Li, Yong Wu, Li-Sheng Ding, Ying-Chun Chen

Index: Chem. Commun. (Camb.) (22) , 2228-30, (2007)

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Abstract

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.