Kinetic Resolution of α‐Hydroxyamide via N‐Heterocyclic Carbene‐Catalyzed Acylation. Issue 10 (9th September 2022)

• Record Type: Journal Article
• Authors: Yamada, Ken‐ichi; Yamauchi, Akiho; Fujiwara, Tatsuya; Hashimoto, Keiji; Wang, Yinli; Kuwano, Satoru; Inokuma, Tsubasa
• Is Part Of: Asian journal of organic chemistry. Volume 11:Issue 10(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-09-09
• Subjects: acylation -- α-hydroxyamide -- catalytic kinetic resolution -- N-heterocyclic carbene -- organocatalysis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202200452
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: The effect of N‐substituent of α‐hydroxyamides on the performance of chiral N‐heterocyclic carbene‐catalyzed kinetic resolution was examined. N ‐ tert ‐Butyl‐α‐hydroxyamides provided the best performance and underwent enantioselective acylation with α‐bromo aldehyde by chiral N‐heterocyclic carbene/carboxylate anion co‐catalysis to realize kinetic resolution in high selectivity factor up to 128. Abstract : The effect of N‐substituent of α‐hydroxyamides on the performance of chiral N‐heterocyclic carbene‐catalyzed kinetic resolution was examined. N ‐ tert ‐Butyl‐α‐hydroxyamides provided the best performance and underwent enantioselective acylation with α‐bromo aldehyde by chiral N‐heterocyclic carbene/carboxylate anion co‐catalysis to realize kinetic resolution in high selectivity factor up to 128.