使用手性P,N配体的喹诺酮类化合物的对映选择性铜催化炔基化反应
Enantioselective Copper-Catalyzed Alkynylation of Quinolones Using Chiral P,N Ligands.
作者信息
Morgan Dáiríne M, Reid Cian M, Guiry Patrick J
机构信息
Centre for Synthesis and Chemical Biology, Synthesis and Solid State Pharmaceutical Centre, School of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland.
Centre for Synthesis and Chemical Biology, School of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland.
出版信息
J Org Chem. 2024 Feb 2;89(3):1993-2000. doi: 10.1021/acs.joc.3c01944. Epub 2023 Nov 15.
Herein we report a catalytic enantioselective alkynylation of quinolones. In this reaction, quinolones are silylated to form a quinolinium ion which then undergoes an enantioselective attack by a copper acetylide, templated by (,,)-UCD-Phim. This gives alkynylated products (24 examples) in yields of up to 92% and enantioselectivities of up to 97%. This methodology has been applied to the synthesis of two natural products, (+)-cuspareine and (+)-galipinine.
在此，我们报道了喹诺酮的催化对映选择性炔基化反应。在该反应中，喹诺酮被硅烷化形成喹啉鎓离子，然后在(,,)-UCD-Phim的模板作用下，被乙炔铜进行对映选择性进攻。这得到了炔基化产物（24个例子），产率高达92%，对映选择性高达97%。该方法已应用于两种天然产物(+)-库斯帕灵和(+)-加利平宁的合成。
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