Enantioselective Synthesis of Arene cis-Dihydrodiols from 2-Pyrones

被引：37
作者：
Liang, Xiao-Wei [1 ,2 ]
Zhao, Yunlong [1 ,2 ]
Si, Xu-Ge [1 ,2 ]
Xu, Meng-Meng [1 ,2 ]
Tan, Jia-Hao [1 ,2 ]
Zhang, Zhi-Mao [1 ,2 ]
Zheng, Cheng-Gong [1 ,2 ]
Zheng, Chao [3 ]
Cai, Quan [1 ,2 ]
机构：
[1] Fudan Univ, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R China
[2] Fudan Univ, Res Ctr Mol Recognit & Synth, 220 Handan Rd, Shanghai 200433, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 41期
基金：
中国国家自然科学基金;
关键词：
asymmetric catalysis; Diels-Alder reaction; dihydrodiols; retro-Diels-Alder reactions; total synthesis; DIELS-ALDER REACTIONS; CHEMOENZYMATIC TOTAL-SYNTHESIS; ELECTRONICALLY MATCHED 2-PYRONES; ENZYMATIC DIHYDROXYLATION; AROMATIC-HYDROCARBONS; OXIDATIVE-DEGRADATION; OXYGENATED AROMATICS; ASYMMETRIC-SYNTHESIS; MICROBIAL OXIDATION; METHYL COUMALATE;
D O I：
10.1002/anie.201908284
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An enantioselective chemical synthesis of arene cis-dihydrodiols has been realized from 2-pyrones through sequential ytterbium-catalyzed asymmetric inverse-electron-demand Diels-Alder (IEDDA) reaction of 2-pyrones and retro-Diels-Alder extrusion of CO2. By using this strategy, a series of substituted arene cis-dihydrodiols can be obtained efficiently with high enantioselectivity (>99 % ee in many cases). Based on this strategy, efficient and concise asymmetric total syntheses of (+)-MK7607 and 1-epi-(+)-MK7607 were accomplished.
引用
收藏
页码：14562 / 14567
页数：6
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