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.

引用

页数：4

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