Chiral Phosphoric Acid Catalyzed (4+1) Annulation of 3-Diazooxindoles/4-Diazooxisoquinolines with para-Quinone Methides to Access Chiral Spiro[dihydrobenzofuran-2,3′-oxindoles/2,4′-oxisoquinolines]

被引：41

作者：

Wu, You-Cai ^{[1
,2
,3
]}

Cui, Bao-Dong ^{[1
,2
,3
]}

Long, Yan ^{[1
,2
,3
]}

Han, Wen-Yong ^{[1
,2
,3
]}

Wan, Nan-Wei ^{[1
,2
,3
]}

Yuan, Wei-Cheng ^{[4
]}

Chen, Yong-Zheng ^{[1
,2
,3
]}

机构：

[1] Zunyi Med Univ, Sch Pharm, Key Lab Biocatalysis & Chiral Drug Synth Guizhou, Zunyi 563000, Guizhou, Peoples R China

[2] Zunyi Med Univ, Key Lab Basic Pharmacol, Minist Educ, Zunyi 563000, Guizhou, Peoples R China

[3] Zunyi Med Univ, Joint Int Res Lab Ethnomed, Minist Educ, Zunyi 563000, Guizhou, Peoples R China

[4] Chinese Acad Sci, Natl Engn Res Ctr Chiral Drugs, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2021年 / 363卷 / 06期

关键词：

heterocyclic diazo compounds; organocatalysis; (4+1) annulation; metal-free; spiro-dihydrobenzofurans;

D O I：

10.1002/adsc.202001309

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An asymmetric (4+1) annulation of 3-diazooxindoles/4-diazooxisoquinolines with para-quinone methides, catalyzed by a chiral phosphoric acid, has been described. A wide range of spiro[dihydrobenzofuran-2,3 '-oxindoles/2,4 '-oxisoquinoline] derivatives were afforded with excellent diastereo- and enantioselectivities. In this study, the possible reaction pathway was proposed and the synthetic applications were shown by a tenfold scale-up conversion as well as the further transformations into other structurally more complex spirocyclic compounds. The significance of this protocol is highlighted by its metal-free participation with heterocyclic diazo compounds as the direct nucleophile and extremely high efficiency in a straightforward and mild reaction process to access the structurally-diverse spiro-heterocyclic 2,3-dihydrobenzofuran derivatives with good to excellent stereocontrol.

引用

页码：1702 / 1713

页数：12

共 68 条

[1]

[Anonymous], 2007, ANGEW CHEM

[2]

[Anonymous], CCDC 2258385

[3] Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory investigations of intramolecular Heck reactions of (E)-α,β-Unsaturated 2-haloanilides and analogues to form enantioenriched spirocyclic products [J].