Enantioselective Cobalt-Catalyzed Sequential Nazarov Cyclization/Electrophilic Fluorination: Access to Chiral α-Fluorocyclopentenones

被引：29
|
作者：
Zhang, Heyi [1 ]
Cheng, Biao [1 ]
Lu, Zhan [1 ]
机构：
[1] Zhejiang Univ, Dept Chem, Hangzhou 310058, Zhejiang, Peoples R China
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 13期
基金：
中国国家自然科学基金;
关键词：
ASYMMETRIC FLUORINATION; BETA-KETOESTERS; MEDICINAL CHEMISTRY; RECENT PROGRESS; KETO-ESTERS; CYCLIZATION; TRIFLUOROMETHYLATION; CYCLOPENTENONES; CONSTRUCTION; DERIVATIVES;
D O I：
10.1021/acs.orglett.8b01597
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A newly designed thiazoline iminopyridine ligand for enantioselective cobalt-catalyzed sequential Nazarov cyclization/electrophilic fluorination was developed. Various chiral alpha-fluorocyclopentenones were prepared with good yields and diastereo- and enantioselectivities. Further derivatizations could be easily carried out to provide chiral cyclopentenols with three contiguous stereocenters. Furthermore, a direct deesterification of fluorinated products could afford chiral alpha-single fluorine-substituted cyclopentenones.
引用
收藏
页码：4028 / 4031
页数：4
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