1569076-60-3Relevant articles and documents
A short asymmetric synthesis of octahydroindole derivatives by application of catalytic C(sp3)-H amination reaction
Mazurais, Marie,Lescot, Camille,Retailleau, Pascal,Dauban, Philippe
, p. 66 - 79 (2014)
The stereoselective synthesis of octahydroindole derivatives is reported according to 3-4-step sequences. The strategy relies on our previously developed catalytic asymmetric C(sp3)-H amination reaction. Its application to cyclic enol triflates affords allylic amines in good yields and stereoselectivity. The C-H functionalization step, then, is followed by a Heck coupling reaction, a Mitsunobu reaction and a final intramolecular cycloaddition reaction thereby leading to the isolation of the expected heterocyclic compounds with an overall yield of up to 69 %. In addition, the chirality introduced in the intermolecular C(sp3)-H amination reaction allows controlling the configuration of the three other stereocenters created in the intramolecular cycloaddition reaction. A second sequence starts from benzocyclobutene and affords fused benzo-octahydroindole derivatives over three steps. The short stereoselective synthesis of octahydroindole derivatives is reported. Catalytic asymmetric C(sp3)-H amination reactions and stereoselective intramolecular cycloaddition reactions are the key steps of the strategy that affords an efficient versatile access to molecular diversity. Copyright
