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

Organic & Biomolecular Chemistry Pub Date: 2016-07-04 DOI: 10.1039/C6OB01152G

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.

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