Copper-Catalyzed Regio- and Stereoselective Ring-Opening of Cyclic Sulfamidates with Grignard Reagents assisted by Lithium Chloride

Copper‐catalyzed ring‐opening reactions of cyclic 1,2‐sulfamidates with a wide range of Grignard reagents have been investigated. The use of lithium chloride as an additive is essential to activate CO bond cleavage. The reaction represents highly regio‐ and stereoselective, and thus allows for effi...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2015-06, Vol.357 (9), p.2027-2032
Main Authors: Arigala, Pitchaiah, Sadu, Venkata S., Hwang, In-Taek, Hwang, Jin-Soo, Kim, Chul-Ung, Lee, Kee-In
Format: Article
Language:English
Subjects:
Additives
Bonding
Catalysis
Cleavage
CuI/LiCl
Derivatives
inversion
Lithium chlorides
ring-opening
sulfamidate
Synthesis
α-branched benzylamine
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Summary:Copper‐catalyzed ring‐opening reactions of cyclic 1,2‐sulfamidates with a wide range of Grignard reagents have been investigated. The use of lithium chloride as an additive is essential to activate CO bond cleavage. The reaction represents highly regio‐ and stereoselective, and thus allows for efficient synthesis of enantioenriched α‐branched benzylamine derivatives. Furthermore, we demonstrated that the products are potential to be used as building blocks for the preparation of wide range of nitrogen‐containing heterocycles.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201400850