Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstraße 21, 79104, Freiburg im Breisgau, Germany.
Angew Chem Int Ed Engl. 2019 Mar 11;58(11):3378-3381. doi: 10.1002/anie.201812984. Epub 2019 Jan 29.
A complementing Pd- and Rh-catalyzed dynamic kinetic resolution (DKR) of racemic allenes leading to N-allylated pyrazoles is described. Such compounds are of enormous interest in medicinal chemistry as certified drugs and potential drug candidates. The new methods feature high chemo-, regio- and enantioselectivities aside from displaying a broad substrate scope and functional group compatibility. A mechanistic rational accounting for allene racemization and trans-alkene selectivity is discussed.
描述了手性丙二烯的钯和铑催化动态动力学拆分(DKR),得到的 N-烯丙基吡唑化合物在药物化学中具有巨大的应用价值,包括已上市药物和潜在药物候选物。除了具有广泛的底物范围和官能团兼容性外,这些新方法还具有高的化学选择性、区域选择性和对映选择性。讨论了对丙二烯外消旋化和反式烯烃选择性的机械合理性。