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Novel strategies for catalytic asymmetric synthesis of C1-chiral 1,2,3,4-tetrahydroisoquinolines and 3,4-dihydrotetrahydroisoquinolines

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 2, Issue 3, Pages 288-299

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4qo00294f

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Funding

  1. National Nature Science Foundation of China [21402025, 21102016]
  2. National Basic Research Program of China (973 Program) [2012CB720300]
  3. Northeast Normal University
  4. Shanghai Rising-Star Program [14QA1400500]
  5. Shanghai Scientific and Technological Innovation Project [13520711500]

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1,2,3,4-Tetrahydroisoquinoline is one of the most important privileged scaffolds present in natural products. C1-chiral tetrahydroisoquinolines have exhibited a wide variety of bioactivities and found applications as chiral scaffolds in asymmetric catalysis. This paper summarizes novel catalytic stereoselective strategies that emerged in the last ten years for synthesis of 1,2,3,4-tetrahydroisoquinoline and 3,4-dihydroisoquinoline scaffolds, beyond the traditional Pictet-Spengler and related protocols, as well as their applications in the total synthesis of alkaloid natural products.

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