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
收藏
页码：182 / 185
页数：4
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