Enantioselective Copper-Catalyzed Alkynylation of Quinolones Using Chiral P,N Ligands

被引：2

作者：

Morgan, Dairine M. ^{[1
]}

Reid, Cian M. ^{[2
]}

Guiry, Patrick J. ^{[1
]}

机构：

[1] Univ Coll Dublin, Sch Chem, Synth & Solid State Pharmaceut Ctr, Ctr Synth & Chem Biol, Dublin 4, Ireland

[2] Univ Coll Dublin, Sch Chem, Ctr Synth & Chem Biol, Dublin 4, Ireland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 89卷 / 03期

基金：

爱尔兰科学基金会;

关键词：

ASYMMETRIC HYDROGENATION; ALKYNES; ROUTE;

D O I：

10.1021/acs.joc.3c01944

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 (S,S,R-a)-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.

引用

页码：1993 / 2000

页数：8

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