Highly enantioselective δ-protonation and formal [3+3] annulation promoted by N-heterocyclic carbene

被引：9

作者：

Dong, Mengdie ^{[1
]}

Duan, Xiao-Yong ^{[1
,2
]}

Li, Yanting ^{[1
]}

Liu, Binghao ^{[1
]}

Qi, Jing ^{[1
,2
]}

机构：

[1] Hebei Univ, Coll Chem & Environm Sci, Key Lab Chem Biol Hebei Prov, Baoding 071002, Peoples R China

[2] Hebei Univ, Key Lab Med Chem & Mol Diag, Minist Educ, Baoding 071002, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 11期

基金：

中国国家自然科学基金;

关键词：

CATALYTIC ASYMMETRIC PROTONATION; BETA-PROTONATION; TRANSFER HYDROGENATION; COOPERATIVE CATALYSIS; ACTIVATION; ENALS;

D O I：

10.1039/d2qo00257d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An N-heterocyclic carbene (NHC) catalyzed highly enantioselective delta-protonation of alpha,beta-gamma,delta-diunsaturated aldehydes is described. In this work, a chiral NHC catalyst reacts with alpha,beta-gamma,delta-diunsaturated aldehydes to generate the extended Breslow intermediate. Upon highly enantioselective delta-protonation and tautomerization, the resulting alpha,beta-unsaturated acyl azolium undergoes a [3 + 3] annulation with enamines to afford various dihydropyridinones with excellent enantioselectivities and good yields (up to 99% ee). This unique intermediate also provides access to delta-chiral esters with potential enantioselectivities.

引用

页码：3039 / 3044

页数：6

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