Ir‐Catalyzed Enantioconvergent Synthesis of Diversely Protected Allenylic Amines Employing Ammonia Surrogates

The first iridium catalyzed, enantioconvergent amination of allenylic carbonates is reported. This process utilizes various commercially available carbamates and sulfonamides to generate allenylic amines including commonly employed protected groups (Boc, Fmoc, Cbz, Ts, Ns) in 62–82 % yield and 87–98...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2020-09, Vol.59 (38), p.16404-16408
Main Authors: Glatz, Fabian, Petrone, David A., Carreira, Erick M.
Format: Article
Language:English
Subjects:
allenes
Amination
Amines
Ammonia
Carbamates (tradename)
Carbonates
Chemical synthesis
enantioconvergent catalysis
heterocycles
Iridium
Sulfonamides
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Summary:The first iridium catalyzed, enantioconvergent amination of allenylic carbonates is reported. This process utilizes various commercially available carbamates and sulfonamides to generate allenylic amines including commonly employed protected groups (Boc, Fmoc, Cbz, Ts, Ns) in 62–82 % yield and 87–98 % ee. The products generated through this scalable procedure serve as effective linchpins for the rapid, enantiospecific synthesis of a wide range of complex structures. Pick and choose: Ir catalysis enables, for the first time, the synthesis of diversely protected allenylic amines employing readily available ammonia equivalents. This convenient method is scalable and with access to these building blocks in high enantiomeric excess, a variety of optically active heterocycles may be prepared which incorporate commonly used amine protecting groups.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202005599