Catalytic cascade aldol-cyclization of tertiary ketone enolates for enantioselective synthesis of keto-esters with a C-F quaternary stereogenic center

被引：28
作者：
Sha, Wanxing [1 ]
Zhang, Lijun [1 ]
Zhang, Wenzhong [1 ]
Mei, Haibo [1 ]
Soloshonok, Vadim A. [2 ,3 ]
Han, Jianlin [1 ]
Pan, Yi [1 ]
机构：
[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China
[2] Univ Basque Country UPV EHU, Fac Chem, Dept Organ Chem 1, Paseo Manuel Lardizabal 3, San Sebastian 20018, Spain
[3] Basque Fdn Sci, IKERBASQUE, Alameda Urquijo 36-5,Plaza Bizkaia, Bilbao 48011, Spain
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 30期
基金：
中国国家自然科学基金;
关键词：
SELF-DISPROPORTIONATION; ACHIRAL CHROMATOGRAPHY; OPTICAL PURIFICATIONS; MEDICINAL CHEMISTRY; CRYPHONECTRIC ACID; FLUORINE CHEMISTRY; LYNGBYA-MAJUSCULA; PITIPEPTOLIDE-A; ENANTIOMERS; CONSTRUCTION;
D O I：
10.1039/c6ob01152g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first asymmetric catalytic aldol-cyclization reaction of detrifluoroacetylatively in situ generated enolates with methyl 2-formylbenzoate is reported. This reaction tolerates a wide range of substrates, affording fluorinated quaternary stereogenic alpha,alpha-dialkyl/cyclo-alkyl-beta-ketoesters with good yields, high diastereo- (94% de) and enantioselectivity (96% ee) at room temperature.
引用
收藏
页码：7295 / 7303
页数：9
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