Organocatalytic aldol and domino Michael-aldol reactions of α,α-difluoro-β-keto esters with acetone

•Efficient organocatalyzed reactions of α,α-difluoro-β-keto esters with acetone were investigated.•α,α-Difluoro-β-keto ester could include various functional groups.•The high diastereoselectivity was obtained.

Organocatalyzed reactions of α,α-difluoro-β-keto esters with acetone were demonstrated. In the presence of L-proline, the Aldol reaction occurred under mild conditions to give the corresponding tertiary α,α-difluoroalcohols in good yields with high enantioselectivities. Using pyrrolidine as catalyst, the domino Michael-aldol reaction took place readily to give the corresponding addition products in high yields with excellent diastereoselectivities.

Graphical abstractSynopsis: In the reactions of α,α-difluoro-β-keto esters with acetone, both aldol reaction and domino Michael-aldol reaction could tolerate a broad range of functional groups and give the corresponding products in high stereoselectivity.Figure optionsDownload full-size imageDownload as PowerPoint slide