Kinetic Resolution of α-Hydroxyamide via N-Heterocyclic Carbene-Catalyzed Acylation

被引：9
|
作者：
Yamada, Ken-ichi [1 ,2 ]
Yamauchi, Akiho [1 ]
Fujiwara, Tatsuya [1 ]
Hashimoto, Keiji [1 ]
Wang, Yinli [1 ,3 ]
Kuwano, Satoru [3 ]
Inokuma, Tsubasa [1 ,2 ]
机构：
[1] Tokushima Univ, Grad Sch Pharmaceut Sci, Shomachi, Tokushima 7708505, Japan
[2] Tokushima Univ, Res Cluster Innovat Chem Sensing, Shomachi, Tokushima 7708505, Japan
[3] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 11卷 / 10期
关键词：
acylation; alpha-hydroxyamide; catalytic kinetic resolution; N-heterocyclic carbene; organocatalysis; CARBOXYLIC-ACIDS; AMINO-ALCOHOLS; LEAVING GROUP; DERIVATIVES; CYCLIZATION; CONVERSION;
D O I：
10.1002/ajoc.202200452
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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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页数：4
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