N-Heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: Efficient synthesis of α-amino-β-keto esters

被引：13

作者：

Uno, Takuya ^{[1
]}

Kobayashi, Yusuke ^{[1
]}

Takemoto, Yoshiji ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 8卷

关键词：

alpha-amino-beta-keto esters; cross-aza-benzoin; alpha-imino ester; N-heterocyclic carbenes; organocatalysis; umpolung reactions; SELECTIVE ASYMMETRIC HYDROGENATION; DYNAMIC KINETIC RESOLUTION; ENANTIOSELECTIVE SYNTHESIS; ALDEHYDES; ACYLATION; AMINOKETONES;

D O I：

10.3762/bjoc.8.169

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient catalytic synthesis of alpha-amino-beta-keto esters has been newly developed. Cross-coupling of various aldehydes with alpha-imino ester, catalyzed by N-heterocyclic carbene, leads chemoselectively to alpha-amino-beta-keto esters in moderate to good yields with high atom efficiency. The reaction mechanism is discussed, and it is proposed that the alpha-amino-beta-keto esters are formed under thermodynamic control.

引用

页码：1499 / 1504

页数：6

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