Synthesis 2020; 52(22): 3337-3355
DOI: 10.1055/s-0040-1707206
short review
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of C1-Chiral THIQs with Imines in Isoquinoline Rings

Dan Li
a  School of Pharmaceutical Sciences, Capital Medical University, No. 10 Xitoutiao You An Men Street, Beijing 100069, P. R. of China   Email: lidan19@ccmu.edu.cn   Email: weigao@ccmu.edu.cn
,
Xiaochao Chen
b  School of Traditional Chinese Medicine, Capital Medical University No. 10, Xitoutiao You An Men Street, Beijing 100069, P. R. of China
,
Wei Gao
a  School of Pharmaceutical Sciences, Capital Medical University, No. 10 Xitoutiao You An Men Street, Beijing 100069, P. R. of China   Email: lidan19@ccmu.edu.cn   Email: weigao@ccmu.edu.cn
b  School of Traditional Chinese Medicine, Capital Medical University No. 10, Xitoutiao You An Men Street, Beijing 100069, P. R. of China
› Author Affiliations
We gratefully thank Capital Medical University and the Natural Science Foundation of China (No. 81773830) for financial support.
Further Information

Publication History

Received: 29 May 2020

Accepted after revision: 29 June 2020

Publication Date:
28 July 2020 (online)


Abstract

Tetrahydroisoquinoline (THIQ) scaffolds are important structural units that widely exist in a variety of natural alkaloids and synthetic analogues. Asymmetric synthesis of C1-chiral THIQ is of particular importance due to its significant pharmaceutical, agrochemical, and other biological activities, and the usually distinct bioactivities exhibited by the two enantiomers. In this review, we highlight the significant advances achieved in this field, present recent asymmetric synthesis with imines in isoquinoline rings ordered according to the sequence of various substrate types. New strategies could be inspired and more types of substrates need further development.

1 Introduction

2 Catalytic Asymmetric Reaction of Dihydroisoquinolines

2.1 Asymmetric Reactions of 3,4-Dihydroisoquinolines

2.2 Asymmetric Reactions of Dihydroisoquinolinium Salts

2.3 Asymmetric Reactions of C,N-Cyclic N′-Acyl Azomethine Imines

2.3.1 NED [3+2] Cycloaddition of C,N-Cyclic N′-Acyl Azomethine Imines

2.3.2 IED [3+2] Cycloaddition of C,N-Cyclic N′-Acyl Azomethine Imines

2.3.3 [3+3] Cycloaddition of C,N-Cyclic N′-Acyl Azomethine Imines

2.3.4 [4+3] Cycloaddition of C,N-Cyclic N′-Acyl Azomethine Imines

2.3.5 Asymmetric Addition Reactions to C,N-Cyclic N′-Acyl Azomethine Imines

2.4 Asymmetric Reactions of C,N-Cyclic Nitrones

3 Catalytic Asymmetric Mannich Reactions of Isoquinolines

4 Conclusions and Perspectives

 
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