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Synthesis 2020; 52(22): 3337-3355
DOI: 10.1055/s-0040-1707206
DOI: 10.1055/s-0040-1707206
short review
Asymmetric Synthesis of C1-Chiral THIQs with Imines in Isoquinoline Rings
We gratefully thank Capital Medical University and the Natural Science Foundation of China (No. 81773830) for financial support.Weitere Informationen
Publikationsverlauf
Received: 29. Mai 2020
Accepted after revision: 29. Juni 2020
Publikationsdatum:
28. Juli 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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Selected reviews of iridium-catalyzed asymmetric hydrogennation of imines:
For recent reviews, see:
For reviews on the diverse chemistry of azlactones, see:
For selected examples, see:
For selected 1,3-DCs of azlactones, see:
For selected examples, see: