Pharmacological evaluation of 2-amino-6(7)- and 9-amino-6-trifluoromethylbenzonorbornenes, the conformationally rigid analogues of norfenfluramine in mice

Organocatalytic Enantioselective Higher‐Order Cycloadditions of In Situ Generated Amino Isobenzofulvenes

“…Theattained benzonorbornenes 4 contain five contiguous stereocenters and the scaffold is of interest because of its presence in commercial pesticides and neurotransmitter analogues. [8] Following optimization of the reaction conditions (see the Supporting Information), the catalyst 3 (20 mol %), in the presence of p-methyl-benzoic acid (20 mol %) in CDCl 3 , facilitated the formation of the benzonorbornene 4a from the indene 1a and nitrostyrene (2a; 2.0 equiv) in good yield and high enantioselectivity ( Table 1, entry 1). Forp urification purposes,the alcohols 5 were isolated after one-pot reduction of the aldehyde [8+ +2]-adducts 4.I na ll entries only one diastereoisomer was observed with small amounts (< 5%)of aMichael adduct (not shown).…”