Enantioselective Synthesis of Chromanones through Organocatalytic Tandem Reactions

被引：9

作者：

Lu, Mengxue ^{[1
,2
]}

Wang, Xin ^{[1
,2
]}

Xiong, Zongli ^{[1
,2
]}

Duan, Jingxiang ^{[1
,2
]}

Ren, Wen ^{[1
,2
]}

Yao, Weijun ^{[3
]}

Xia, Yi ^{[1
,2
]}

Wang, Zhen ^{[1
,2
]}

机构：

[1] Chongqing Univ, Sch Pharmaceut Sci, Chongqing 401331, Peoples R China

[2] Chongqing Univ, Chongqing Key Lab Nat Drug Res, Chongqing 401331, Peoples R China

[3] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310018, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 23期

基金：

中国国家自然科学基金;

关键词：

chiral chromanones; enantioselective synthesis; iminium catalysis; 1; 3-diketones; tandem reactions; ONE-POT SYNTHESIS; ASYMMETRIC-SYNTHESIS; BETA-KETOCARBONYLS; QUINONE METHIDES; FLAVANONES; TRANSFORMATIONS; STEREOCENTERS; HYDROGENATION; CHROMONES; REAGENTS;

D O I：

10.1002/adsc.202001031

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An enantioselective approach to lactone-fused chromanone derivatives from 1-(2-hydroxyaryl)-1,3-diketones and alpha,beta-unsaturated aldehydes under mild conditions has been developed, which included organocatalytic stepwise Michael addition/ cycloketalization/hemiacetalization and followed by oxidation reaction. In the presence of chiral amine organocatalyst and an additional salicylic acid, a wide range of 1-(2-hydroxyaryl)-1,3-diketones and alpha,beta-unsaturated aldehydes were tolerated, furnishing a spectrum of lactone-fused tricyclic chromanones bearing three contiguous stereocenters in high yields with good to excellent selectivities (90->99% ee, >19:1 d.r.).

引用

页码：5524 / 5528

页数：5

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