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Application of a Catalytic Asymmetric Povarov Reaction using Chiral Ureas to the Synthesis of a Tetrahydroquinoline Library.
|Publication Type||Journal Article|
|Authors||Gerard, B., O'Shea MW, Donckele E., Kesavan S., Akella LB, Xu H., Jacobsen EN, and Marcaurelle LA|
|Abstract||A 2328-membered library of 2,3,4-trisubstituted tetrahydroquinolines was produced using a combination of solution- and solid-phase synthesis techniques. A tetrahydroquinoline (THQ) scaffold was prepared via an asymmetric Povarov reaction using cooperative catalysis to generate three contiguous stereogenic centers. A matrix of 4 stereoisomers of the THQ scaffold was prepared to enable the development of stereo/structure-activity relationships (SSAR) upon biological testing. A sparse matrix design strategy was employed to select library members to be synthesized with the goal of generating a diverse collection of tetrahydroquinolines with physicochemical properties suitable for downstream discovery.|
|Year of Publication||2012|
|Journal||ACS combinatorial science|
|Date Published (YYYY/MM/DD)||2012/10/22|