An expedient synthesis of α,α-difluoro-β-hydroxy ketones via decarboxylative aldol reaction of α,α-difluoro-β-keto acids with aldehydes

• Published in: Tetrahedron letters Vol. 58; no. 34; pp. 3394 - 3397
• Main Authors: Huang, Da-Kang, Lei, Zhong-Liang, Zhu, Yu-Jun, Liu, Zhen-Jiang, Hu, Xiao-Jun, Mao, Hai-Fang
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 23.08.2017; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Decarboxylative aldol reaction; Physical Sciences; Science & Technology; α,α-Difluoro-β-hydroxy ketone; α,α-Difluoro-β-keto acid; α,α-Difluoro-β-hydroxy ketone; Decarboxylative aldol reaction; α,α-Difluoro-β-keto acid; HALF THIOESTERS; ASYMMETRIC-SYNTHESIS; 3-HYDROXY OXINDOLES; CARBON-CARBON BONDS; KETOACIDS; alpha,alpha-Difluoro-beta-hydroxy ketone; alpha,alpha-Difluoro-beta-keto acid; N-SULFINYL METALLOENAMINES; ADDITION-REACTIONS; BETA-HYDROXY KETONES; POLYKETIDE BIOSYNTHESIS; ALPHA,BETA-UNSATURATED TRIFLUOROMETHYL KETONES
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2017.07.060

[Display omitted] •First decarboxylative aldol reaction of α,α-difluoro-β-keto acids with aldehydes.•Highly convenient, yet efficient base- and metal-free process.•Structurally diverse α,α-difluoro-β-hydroxy ketones were obtained in high yields. A novel decarboxylative aldol reaction of α,α-difluoro-β-keto acids with aldehydes in the absence of any base and metal catalysts has been developed. This reaction provides a highly convenient and efficient method for the synthesis of structurally diverse α,α-difluoro-β-hydroxy ketones in good to excellent yields.