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Intramolecular Redox‐Mannich Reactions: Facile Access to the Tetrahydroprotoberberine Core
Author(s) -
Ma Longle,
Seidel Daniel
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501667
Subject(s) - chemistry , redox , intramolecular force , amine gas treating , pyrrolidine , mannich reaction , alkylation , combinatorial chemistry , epimer , organic chemistry , catalysis
Abstract Cyclic amines such as pyrrolidine undergo redox‐annulations with 2‐formylaryl malonates. Concurrent oxidative amine α‐CH bond functionalization and reductive N‐alkylation render this transformation redox‐neutral. This redox‐Mannich process provides regioisomers of classic Reinhoudt reaction products as an entry to the tetrahydroprotoberberine core, enabling the synthesis of (±)‐thalictricavine and its epimer. An unusually mild amine‐promoted dealkoxycarbonylation was discovered in the course of these studies.