Catalytic Enantioselective Allylation of Acetylenic Aldehydes by Chiral Phosphoric Acid/Transition Metal Cooperative Catalysis: Formal Synthesis of Fostriecin
Catalytic Enantioselective Allylation of Acetylenic Aldehydes by Chiral Phosphoric Acid/Transition Metal Cooperative Catalysis: Formal Synthesis of Fostriecin
复制标题
手性磷酸/过渡金属协同催化乙醛的对映选择性烯丙基化：磷三菌素的形式合成
DOI：
10.1021/acs.orglett.1c01166
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发表时间：
2021
期刊：
影响因子：
5.2
通讯作者：
Terada Masahiro
中科院分区：
文献类型：
--
作者：
Umemiya Shigenobu;Terada Masahiro
研究了手性磷酸/过渡金属协同催化硅取代炔醛的不对称烯丙基化反应。在温和的条件下，以良好的产率和优异的对映选择性（> 99%ee）获得了对映体富集的高烯丙基炔丙醇。此外，本发明的不对称选择性烯丙基化反应作为关键步骤，实现了最短的福曲星的正式合成。McDonald等人报道的已知的磷霉素中间体仅用9步合成，总收率为39%。
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.