Laboratoire de Chimie Organique , Institute of Chemistry, Biology and Innovation (CBI), ESPCI Paris/CNRS/PSL Research University , 10 rue Vauquelin , 75231 Paris Cedex 05, France.
Queen Mary University of London , School of Biological and Chemical Sciences , Mile End Road , London , E1 4NS , U.K.
Org Lett. 2019 Feb 1;21(3):603-607. doi: 10.1021/acs.orglett.8b03613. Epub 2019 Jan 15.
The synthesis of chiral unsaturated γ-lactams is reported featuring a highly enantioselective palladium-catalyzed asymmetric allylic alkylation of α,γ-disubstituted 2-silyloxypyrroles. This method allows a straightforward access to optically active γ-lactams bearing an α-quaternary stereogenic center in high yields (up to 93%), high regioselectivities (up to >20:1), and excellent enantioselectivities (up to 95% ee). To further demonstrate the synthetic utility of the method, the resulting allylated products were converted to various versatile chiral building blocks, such as pyrrolidines and pyrrolidinones.
报道了一种通过手性不饱和γ-内酰胺的合成，其特征在于钯催化的高度对映选择性烯丙基烷基化α，γ-二取代的 2-硅氧基吡咯。该方法可以直接获得光学活性的γ-内酰胺，其中含有α-季立体中心，产率高（高达 93%），区域选择性高（高达>20:1），对映选择性高（高达 95%ee）。为了进一步证明该方法的合成实用性，得到的烯丙基化产物被转化为各种多功能的手性构建块，如吡咯烷和吡咯烷酮。
