Synthesis of Chiral 3H-Pyrrolo[1,2-a]indoles Via Organocatalytic Enantioselective Addition of Alkynyl Biphenyl Quinone Methides

被引：1
|
作者：
Pan, Sheng [1 ]
Wang, Xing [1 ]
Liu, Meiwen [2 ]
Fang, Fang [2 ]
Xia, Yan [1 ]
Li, Pengfei [2 ]
Li, Wenjun [1 ]
机构：
[1] Qingdao Univ, Sch Pharm, Dept Med Chem, Qingdao 266021, Shandong, Peoples R China
[2] Southern Univ Sci & Technol SUSTech, Southern Univ Sci & Technol, Guangming Adv Res Inst, Coll Sci,Dept Chem,Guangdong Prov Key Lab Catalysi, Shenzhen 518055, Peoples R China
来源：
CHEMCATCHEM | 2024年 / 16卷 / 21期
关键词：
Addition; Biphenyl quinone methide; Chiral phosphoric acid; Indole; Propargyl alcohol; CATALYTIC ASYMMETRIC REACTIONS; ACCESS;
D O I：
10.1002/cctc.202400900
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
An organocatalytic enantioselective reaction utilizing alpha-[4-(4-hydroxyphenyl)phenyl]propargyl alcohols and 3-substituted indoles has been successfully established for the synthesis of chiral 3H-pyrrolo[1,2-a]indoles. Through the assistance of an appropriate chiral phosphoric acid, a cascade sequence is facilitated, beginning with the dehydration of alpha-[4-(4-hydroxyphenyl)phenyl]propargyl alcohols to form alkynyl 4,4'-biphenyl quinone methides (4,4'-BQMs). Subsequently, 1,12-addition of 3H-pyrrolo[1,2-a]indoles to these alkynyl 4,4'-BQMs results in the formation of allenes, which are then protonated and regenerate 4,4'-BQMs. Finally, an enantioselective intramolecular annulation of 4,4'-BQMs occurs smoothly, leading to the production of a range of 3H-pyrrolo[1,2-a]indoles with high efficiency and asymmetric induction.
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页数：7
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