Forskning ved Københavns Universitet - Københavns Universitet

Forside

Diversity-Oriented Syntheses by Combining CuAAC and Stereoselective INCIC Reactions with Peptides

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningfagfællebedømt

Cascade reactions proceeding through peptide-derived N-carbamoyl iminium ions are reported. Two new reactions of N-carbamoyl iminium ions are described, including a stereoselective double cyclization generating N,N′-aminals and an acid-promoted auto-oxidation. Mechanistic investigations revealed that the N,N′-aminal formation is reversible under strongly acidic conditions. Both of these new reactions proved to be completely orthogonal to subsequent CuAAC chemistry. The reactions were performed in solution and on solid support. The robustness and high stereoselectivity of the methodology holds great promise for applications in parallel diversity-oriented synthesis and in combinatorial synthesis for drug screening.

OriginalsprogEngelsk
TidsskriftChemistry - A European Journal
Vol/bind23
Udgave nummer56
Sider (fra-til)13869–13874
Antal sider6
ISSN0947-6539
DOI
StatusUdgivet - 2017

ID: 184355665