Iridium-Catalyzed Asymmetric Cascade Allylation/Pictet-Spengler Cyclization Reaction for the Enantioselective Synthesis of 1,3,4-Trisubstituted Tetrahydroisoquinolines

被引：8

作者：

Yang, Wu-Lin ^{[1
,2
]}

Liu, Tian-Tian ^{[1
,2
]}

Ni, Tao ^{[1
,2
]}

Zhu, Bin ^{[3
,4
]}

Luo, Xiaoyan ^{[1
,2
]}

Deng, Wei-Ping ^{[1
,2
]}

机构：

[1] East China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China

[2] East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Shanghai 200237, Peoples R China

[3] East China Univ Sci & Technol, Engn Res Ctr Pharmaceut Proc Chem, State Key Lab Bioreactor Engn, Minist Educ, Shanghai 200237, Peoples R China

[4] East China Univ Sci & Technol, Sch Pharm, Lab Pharmaceut Crystal Engn & Technol, Shanghai 200237, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 07期

基金：

中国国家自然科学基金;

关键词：

ALLYLIC ALCOHOLS; ABSOLUTE-CONFIGURATION; AZOMETHINE YLIDES; DUAL CATALYSIS; CYCLIC IMINES; HYDROGENATION; ACID; CYCLOADDITIONS; CONSTRUCTION; DERIVATIVES;

D O I：

10.1021/acs.orglett.1c00709

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An iridium-catalyzed trifluoroacetic acid-promoted asymmetric cascade allylation/Pictet-Spengler cyclization reaction of azomethine ylides with aromatic allylic alcohols is reported. This protocol provides a facile and scalable method for the construction of 1,3,4-trisubstituted tetrahydroisoquinolines containing two stereogenic centers in good yields (up to 96%) with generally excellent diastereo- and enantioselectivities (up to >20:1 dr and >99% ee). Furthermore, a series of aromatic heterocyclefused piperidines were also obtained with excellent enantiocontrol by this methodology.

引用

页码：2790 / 2796

页数：7

共 85 条

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