Chiral Amine-Catalyzed Stereoselective [4+2] Annulations of Alkenyl Thiazolones and Aliphatic Aldehydes via a Step-Wise Mechanism

被引：20

作者：

Dai, Qing-Song ^{[1
]}

Zhang, Xiang ^{[1
]}

Yang, Kai-Chuan ^{[1
]}

Li, Mao-Hua ^{[1
]}

Yang, Jie ^{[1
]}

Li, Qing-Zhu ^{[1
]}

Feng, Xin ^{[1
]}

Han, Bo ^{[2
]}

Li, Jun-Long ^{[1
]}

机构：

[1] Chengdu Univ, Antibiot Res & Reevaluat Key Lab Sichuan Prov, Sichuan Ind Inst Antibiot, Chengdu 610052, Sichuan, Peoples R China

[2] Chengdu Univ Tradit Chinese Med, State Key Lab Breeding Base Systemat Res Dev & Ut, Chengdu 611137, Sichuan, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 22期

关键词：

asymmetric annulation; alkenyl thiazolones; aminocatalysis; three-component reaction; step-wise mechanism; N-HETEROCYCLIC CARBENE; DIELS-ALDER REACTIONS; ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE ALDOL REACTIONS; DIARYLPROLINOL SILYL ETHERS; CYCLOADDITION REACTIONS; MICHAEL REACTIONS; MANNICH REACTIONS; HOMO ACTIVATION; ACETALDEHYDE;

D O I：

10.1002/adsc.201800806

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient diastereo- and enantioselective formal oxo-Diels-Alder reaction of enolizable aliphatic aldehydes and 5-alkenyl thiazolones was developed through chiral amine catalysis. With a robust enamine activation strategy, both simple aliphatic aldehydes and a challenging aqueous acetaldehyde could participate well as competent dienophiles in the reaction. A variety of thiazole-fused dihydropyran derivatives were facilely produced in up to 99% yield with up to >99:1 e.r. under mild conditions. Interestingly, a high dosage of the inexpensive aqueous acetaldehyde in a similar catalytic system could lead to a densely functionalized thiazolone product through a three-component cascade reaction, suggesting a step-wise mechanism for the established [4+2] annulation process.

引用

页码：4435 / 4440

页数：6

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