Catalytic cascade aldol–cyclization of tertiary ketone enolates for enantioselective synthesis of keto-esters with a C–F quaternary stereogenic center. Issue 30 (11th July 2016)

• Record Type: Journal Article
• Authors: Sha, Wanxing; Zhang, Lijun; Zhang, Wenzhong; Mei, Haibo; Soloshonok, Vadim A.; Han, Jianlin; Pan, Yi
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 30(2016)
• Page Start: 7295
• Page End: 7303
• Publication Date: 2016-07-11
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob01152g
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The first enantioselective catalytic aldol–cyclization cascade reaction of detrifluoroacetylatively in situ generated tertiary enolates with methyl 2-formylbenzoate is reported. Abstract : 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 α, α-dialkyl/cyclo-alkyl-β-ketoesters with good yields, high diastereo- (94% de) and enantioselectivity (96% ee) at room temperature.