Catalyst-Controlled [3+2] and [4+2] Annulations of Oximes with Propargyl Alcohols: Divergent Access to Indenamines and Isoquinolines

被引：63

作者：

Gong, Wanchun ^{[1
,2
,4
]}

Zhou, Zhi ^{[1
,2
]}

Shi, Jingjing ^{[3
]}

Wu, Bo ^{[1
,2
]}

Huang, Biyun ^{[1
,2
]}

Yi, Wei ^{[1
,2
]}

机构：

[1] Guangzhou Med Univ, Key Lab Mol Clin Pharmacol, Guangzhou 511436, Guangdong, Peoples R China

[2] Guangzhou Med Univ, Affiliated Hosp 5, Guangzhou 511436, Guangdong, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Mat Med, VARI SIMM Ctr, CAS Key Lab Receptor Res,Ctr Struct & Funct Drug, Shanghai 201203, Peoples R China

[4] Shanghai Pharmaceut Holding Co Ltd, Cent Res Inst, Shanghai 201203, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 01期

关键词：

C-H FUNCTIONALIZATION; BOND ACTIVATION; N-OXIDES; ARENES; ISOINDOLINONES; CONSTRUCTION;

D O I：

10.1021/acs.orglett.7b03546

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium(III)- and iridium(III)-catalyzed C-H activation of oximes and coupling with propargyl alcohols is discussed. Depending on the catalyst, the reaction pathway switched between [3 + 2] and [4 + 2] annulation, thus giving divergent access to indenamines and isoquinolines in a one-pot and atom-economical manner. The hydroxyl group in the tertiary propargyl alcohol substrate was found to be crucial in controlling chemoselectivity. Five-membered rhodacycle and iridacycle intermediates have also been identified for mechanism hypotheses.

引用

页码：182 / 185

页数：4

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