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

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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