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Application of a Catalytic Asymmetric Povarov Reaction using Chiral Ureas to the Synthesis of a Tetrahydroquinoline Library.

Publication TypeJournal Article
AuthorsGerard, B., O'Shea MW, Donckele E., Kesavan S., Akella LB, Xu H., Jacobsen EN, and Marcaurelle LA
AbstractA 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 Publication2012
JournalACS combinatorial science
Date Published (YYYY/MM/DD)2012/10/22
ISSN Number2156-8952
DOI10.1021/co300098v
PubMedhttp://www.ncbi.nlm.nih.gov/pubmed/23088641?dopt=Abstract