Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 11, Issue 10, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202200452
Keywords
acylation; alpha-hydroxyamide; catalytic kinetic resolution; N-heterocyclic carbene; organocatalysis
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Funding
- JSPS KAKENHI from MEXT [JP22H05569]
- Sasakawa Scientific Research Grant
- Tokushima University [1802001]
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The effect of N-substituent on the performance of chiral N-heterocyclic carbene-catalyzed kinetic resolution using alpha-hydroxyamides was investigated. N-tert-Butyl-alpha-hydroxyamides exhibited the best performance and achieved enantioselective acylation with alpha-bromo aldehyde through chiral N-heterocyclic carbene/carboxylate anion co-catalysis, leading to a high selectivity factor up to 128.
The effect of N-substituent of alpha-hydroxyamides on the performance of chiral N-heterocyclic carbene-catalyzed kinetic resolution was examined. N-tert-Butyl-alpha-hydroxyamides provided the best performance and underwent enantioselective acylation with alpha-bromo aldehyde by chiral N-heterocyclic carbene/carboxylate anion co-catalysis to realize kinetic resolution in high selectivity factor up to 128.
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