Enantioselective Gold(I)-Catalyzed Heterocyclization-Intermolecular Exo [4+3]-Cycloaddition Reactions for the Synthesis of Chiral Oxa-Bridged Benzocycloheptanes

被引：49
|
作者：
Di, Xiaoyu [1 ]
Wang, Yidong [1 ]
Wu, Lizuo [1 ]
Zhang, Zhan-Ming [1 ]
Dai, Qiang [1 ]
Li, Wenbo [1 ]
Zhang, Junliang [1 ,2 ]
机构：
[1] East China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
[2] Fudan Univ, Dept Chem, 2005 Songhu Rd, Shanghai 2000438, Peoples R China
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 09期
基金：
中国国家自然科学基金;
关键词：
CONTAINING CARBONYL YLIDES; ACID-PROMOTED 3+4; ASYMMETRIC-SYNTHESIS; 4+3 CYCLOADDITIONS; OXYALLYL CATIONS; ALLYL CATIONS; ALKENES; ALLENAMIDES; DERIVATIVES; CYCLIZATION;
D O I：
10.1021/acs.orglett.9b00537
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The highly exo- and enantioselective gold-catalyzed tandem heterocyclization/[4 + 3] cycloaddition of 2-(1-alkynyl)-2-alken-1-ones and 1,3-diphenylisobenzofuran was implemented by utilizing Ming-Phos, which provides a facile access to chiral seven-membered oxa-bridged rings in 80-98% yield with high exo selectivity (exo/endo up to 50:1) and up to 97% ee.
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页码：3018 / 3022
页数：5
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