Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
Org Lett. 2021 May 7;23(9):3767-3771. doi: 10.1021/acs.orglett.1c01166. Epub 2021 Apr 23.
An enantioselective allylation of silyl-substituted acetylenic aldehydes by chiral phosphoric acid (CPA)/transition metal cooperative catalysis was developed. Enantioenriched homoallylic propargyl alcohols were obtained in good yields with excellent enantioselectivities (>99% ee) under mild conditions. Moreover, the shortest formal synthesis of fostriecin was achieved by the present enantioselective allylation protocol as the key step. The known intermediate of fostriecin reported by McDonald and co-worker was synthesized in only nine steps in 39% total yield.
手性磷酸/过渡金属协同催化实现了硅基取代炔基醛的对映选择性烯丙基化反应。在温和条件下，以优异的对映选择性（>99%ee）获得了高收率的同型烯丙基炔丙醇。此外，本对映选择性烯丙基化反应作为关键步骤，实现了福斯特菌素最短的全合成。通过 McDonald 及其同事报道的已知福斯特菌素中间体，以 39%的总收率仅通过 9 步反应即可合成。
