Catalytic Enantioselective Synthesis of N,N‐Acetals from α‐Dicarbonyl Compounds Using Chiral Imidazoline‐Phosphoric Acid Catalysts

The enantioselective synthesis of chiral N,N‐acetals derived from α‐dicarbonyl compounds has been achieved. Good yields and enantioselectivities were observed for the reaction with various α‐dicarbonyl compounds with 2‐aminobenzamides using chiral bis(imidazoline)‐phosphoric acid catalysts. Based on...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2020-12, Vol.362 (23), p.5374-5379
Main Authors: Nakamura, Shuichi, Wada, Tatsumi, Takehara, Tsunayoshi, Suzuki, Takeyuki
Format: Article
Language:English
Subjects:
Acetals
Carbonyl compounds
Catalysts
Chemical synthesis
Enantiomers
Enantioselectivity
Imidazoline
Ketimines
N,N-Acetals
Organic catalysis
Phosphoric acid
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Summary:The enantioselective synthesis of chiral N,N‐acetals derived from α‐dicarbonyl compounds has been achieved. Good yields and enantioselectivities were observed for the reaction with various α‐dicarbonyl compounds with 2‐aminobenzamides using chiral bis(imidazoline)‐phosphoric acid catalysts. Based on these experimental investigations, a possible transition state is proposed to explain the origin of the asymmetric induction.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202001128