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

Dan Li; Xiaochao Chen; Wei Gao

doi:10.1055/s-0040-1707206

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(22): 3337-3355
DOI: 10.1055/s-0040-1707206

short review

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

Dan Li∗

^aSchool 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

^bSchool of Traditional Chinese Medicine, Capital Medical University No. 10, Xitoutiao You An Men Street, Beijing 100069, P. R. of China

,

Wei Gao∗

^aSchool 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

^bSchool of Traditional Chinese Medicine, Capital Medical University No. 10, Xitoutiao You An Men Street, Beijing 100069, P. R. of China

› Institutsangaben

Abstract

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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

Key words

asymmetric catalysis - imines - tetrahydroisoquinoline - dihydroisoquinoline - cyclization - addition

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Referenzen

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