Institute for Organic Chemistry, Albert-Ludwigs-Universität Freiburg, Albertstraße 21, 79104, Freiburg im Breisgau, Germany.
Angew Chem Int Ed Engl. 2020 Dec 21;59(52):23485-23490. doi: 10.1002/anie.202009166. Epub 2020 Oct 26.
A comprehensive study of a diastereoselective Rh-catalyzed cyclization of terminal and internal allenols is reported. The methodology allows the atom economic and highly syn-selective access to synthetically important 2,4-disubstituted and 2,4,6-trisubstituted tetrahydropyrans (THP). Furthermore, its utility and versatility are demonstrated by a great functional-group compatibility and the enantioselective total synthesis of (-)-centrolobine.
本文报道了对末端和内部烯丙醇的非对映选择性 Rh 催化环化的综合研究。该方法允许原子经济性和高 syn-选择性地获得合成上重要的 2,4-二取代和 2,4,6-三取代四氢吡喃(THP)。此外,通过良好的官能团相容性和(-)-centrolobine 的对映选择性全合成证明了其实用性和多功能性。