Enantioselective Synthesis of AG-041R by using N-Heteroarenesulfonyl Cinchona Alkaloid Amides as Organocatalysts

The organocatalytic enantioselective decarboxylative addition of malonic acid half thioesters to ketimines derived from isatins by using N‐heteroarenesulfonyl cinchona alkaloid amides afforded products with high enantioselectivity. The products could be converted into optically active AG‐041R. X‐ray...

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Bibliographic Details
Published in:Chemistry : a European journal 2012-07, Vol.18 (30), p.9276-9280
Main Authors: Hara, Noriyuki, Nakamura, Shuichi, Sano, Masahide, Tamura, Ryota, Funahashi, Yasuhiro, Shibata, Norio
Format: Article
Language:English
Subjects:
Alkaloids
Amides
Amides - chemistry
Catalysis
Chemistry
Cinchona Alkaloids - chemistry
enantioselectivity
Ethers
Hydrogen bonding
Imines
Indoles - chemical synthesis
Indoles - chemistry
ketimines
Molecular Structure
Nitrogen - chemistry
Optical activity
organocatalysis
Quinolines - chemistry
reaction mechanisms
Silver
Stereoisomerism
Sulfhydryl Compounds - chemistry
Thioesters
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Summary:The organocatalytic enantioselective decarboxylative addition of malonic acid half thioesters to ketimines derived from isatins by using N‐heteroarenesulfonyl cinchona alkaloid amides afforded products with high enantioselectivity. The products could be converted into optically active AG‐041R. X‐ray crystallographic analysis revealed that the hydrogen bonding between the sulfonimide proton and the 8‐quinolyl nitrogen atom plays an important role in exerting the enantioselectivity of the reaction. Enantioselective catalysis: The organocatalytic enantioselective decarboxylative addition of malonic acid half thioesters to ketimines affords products with high enantioselectivities (see scheme; CPME=cyclopentyl methyl ether). The products can be converted into optically active AG‐041R. Hydrogen bonding plays an important role in the enantioselectivity of the reaction.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201200367