Synthesis of Oxo-Bridged Dibenzoazocines through Ruthenium-Catalyzed [4+3]-Cycloannulation of Aza-ortho-quinone Methides with Carbonyl Ylides

被引：10

作者：

Jia, Pengfei ^{[1
,2
,3
]}

Lin, Zhiqian ^{[1
,2
,3
]}

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

Liang, Jiao ^{[1
,2
,3
]}

Luo, Cankun ^{[1
,2
,3
]}

Lai, Ruizhi ^{[1
,2
,3
]}

Hai, Li ^{[1
,2
,3
]}

Yang, Zhongzhen ^{[1
,2
,3
]}

Wu, Yong ^{[1
,2
,3
]}

机构：

[1] Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Educ Minist, West China Sch Pharm, Chengdu 610041, Sichuan, Peoples R China

[2] Sichuan Univ, West China Sch Pharm, Dept Med Chem, Sichuan Engn Lab Plant Sourced Drug, Chengdu 610041, Sichuan, Peoples R China

[3] Sichuan Univ, Sichuan Res Ctr Drug Precis Ind Technol, West China Sch Pharm, Chengdu 610041, Sichuan, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 27期

关键词：

DIELS-ALDER REACTIONS; PHOTOASSISTED ACCESS; 1,3-DIPOLAR CYCLOADDITION; CYCLIZATION; ENOLDIAZOACETAMIDES; ANNULATION; IMINES;

D O I：

10.1021/acs.orglett.3c01885

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxo-bridgeddibenzoazocines are furnished within a single syntheticstep at room temperature via ruthenium-catalyzed [4 + 3]-cycloannulationof aza-ortho-quinone methides with carbonyl ylides.Exclusive diastereoselectivity, excellent yield, mild reaction conditions,and broad substrate scope are distinguishing features of this protocol.The product could be prepared on a gram scale and could be furtherfunctionalized into diverse substituted dihydroisobenzofuran derivativesand a dibenzoazocine scaffold.

引用

页码：5134 / 5139

页数：6

共 8 条

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