Manganese‐Catalyzed Carbonylative Annulations for Redox‐Neutral Late‐Stage Diversification

An inexpensive, nontoxic manganese catalyst enabled unprecedented redox‐neutral carbonylative annulations under ambient pressure. The manganese catalyst outperformed all other typically used base and precious‐metal catalysts. The outstanding versatility of the manganese catalysis manifold was reflec...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-05, Vol.57 (19), p.5384-5388
Main Authors: Liang, Yu‐Feng, Steinbock, Ralf, Münch, Annika, Stalke, Dietmar, Ackermann, Lutz
Format: Article
Language:English
Subjects:
Alkaloids
Amino acids
annulation
Carbohydrates
carbonylation
Carbonyls
Catalysis
Catalysts
late-stage modification
Manganese
Natural products
Pressure
Racemization
Steroid hormones
Steroids
Substrates
traceless directing groups
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Summary:An inexpensive, nontoxic manganese catalyst enabled unprecedented redox‐neutral carbonylative annulations under ambient pressure. The manganese catalyst outperformed all other typically used base and precious‐metal catalysts. The outstanding versatility of the manganese catalysis manifold was reflected by ample substrate scope, setting the stage for effective late‐stage manipulations under racemization‐free conditions of a wealth of marketed drugs and natural products, including alkaloids, amino acids, steroids, and carbohydrates. Smart Man: An inexpensive, nontoxic manganese complex catalyzed carbonylative alkyne annulation reactions to form pyrido[1,2‐a]pyrimidin‐4‐ones under ambient pressure. The manganese catalyst outperformed other typically used metal catalysts and showed outstanding versatility, as reflected by the modification of various marketed drugs and natural products, including alkaloids, amino acids, steroids, and carbohydrates.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201801111