Rh(III)-Catalyzed Diastereoselective Annulation of Amides with Quinone Monoacetals: Access to Bridged Nine-Membered Heterocycles via C-H Activation

被引：42
|
作者：
Yang, Wei [1 ,3 ]
Dong, Jinhuan [1 ,2 ]
Wang, Jingyi [2 ]
Xu, Xianxiu [1 ]
机构：
[1] Shandong Normal Univ, Key Lab Mol & Nano Probes, Coll Chem Chem Engn & Mat Sci, Minist Educ, Jinan 250014, Peoples R China
[2] Northeast Normal Univ, Dept Chem, Changchun 130024, Peoples R China
[3] Northeast Elect Power Univ, Coll Chem Engn, Jilin 132012, Jilin, Peoples R China
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 03期
关键词：
ONE-POT SYNTHESIS; N BOND FORMATION; INTERNAL ALKYNES; 8-MEMBERED RINGS; REGIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; 6+2 CYCLOADDITION; ROOM-TEMPERATURE; INDOLE SYNTHESIS; DIAZO-COMPOUNDS;
D O I：
10.1021/acs.orglett.6b03777
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An unprecedented Rh(III)-catalyzed annulation of various benzamides and acrylamides with quinone monoacetals was developed for the facile and efficient one-pot synthesis of bridged nine-membered benzo[dazonine-1,5(2H)-diones and 2-azabicydo [4.3.1]dec-4-ene-3,8-diones. It is the first example of synthesis of nine -membered heterocycles through Rh(III)catalyzed C-H bond functionalization, and both aryl and vinyl C-H bonds are tolerant in this reaction. A plausible mechanism is proposed on the basis of control experiments.
引用
收藏
页码：616 / 619
页数：4
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