The Quinary Catalyst-Substrate Complex Induced Construction of Spiro-Bridged or Cagelike Polyheterocyclic Compounds via a Substrate-Controlled Cascade Process

被引：26

作者：

Wang, Chen ^{[1
]}

Chen, Ying-Han ^{[1
]}

Wu, Hui-Chun ^{[1
]}

Wang, Cong ^{[1
]}

Liu, Yan-Kai ^{[1
,2
]}

机构：

[1] Ocean Univ China, Sch Med & Pharm, Key Lab Marine Drugs, Chinese Minist Educ, Qingdao 266003, Shandong, Peoples R China

[2] Qingdao Natl Lab Marine Sci & Technol, Lab Marine Drugs & Bioprod, Qingdao 266003, Shandong, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 17期

关键词：

ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE CONJUGATE ADDITION; ONE-POT SYNTHESIS; MICHAEL ADDITION; IMINIUM; DERIVATIVES; SPIRO-3,4-DIHYDROPYRANS; CYCLIZATION; DITERPENES; SEQUENCE;

D O I：

10.1021/acs.orglett.9b02375

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric organocatalytic cascade reaction of cyclic beta-oxo aldehydes to 2-hydroxycinnamaldehydes is developed. The bifunctional tertiary amine-thiourea catalyst was used in a rationally designed multiple catalysis where the asymmetric iminium catalysis and thiourea anion-binding catalysis were combined by carboxylate anion as a ternary catalytic system to form a quinary catalyst-substrate complex, providing an efficient protocol for the construction of enantioenriched spiro-bridged or cagelike polyheterocyclic compounds. The reuse of catalysts was also successfully realized.

引用

页码：6750 / 6755

页数：6