Ghosh, Arun K. Banerjee, Shaibal Sinha, Saikat Kang, Soon Bang Zajc, Barbara 2024-01-20T21:31:18Z 2024-01-20T21:31:18Z 2021-09-01 2009-05-15 0022-3263 https://pubs.kist.re.kr/handle/201004/132489 Synthesis and reactivity of N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfonyl)fluoroacetamide, a building block for Julia olefination, is reported. This reagent undergoes condensation reactions with aldehydes and cyclic ketones to give alpha-fluorovinyl Weinreb amides. Olefination reactions proceed under mild, DBU-mediated conditions, or in the presence of NaH. DBU-mediated condensations proceed with either E- or Z-selectivity, depending upon reaction conditions, whereas NaH-mediated reactions are >= 98% Z-stereoselective. Conversion of the Weinreb amide moiety in N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfanyl)fluoroacetamide to ketones, followed by oxidation, resulted in another set of olefination reagents, namely (1,3-benzothiazol-2-ylsulfonyl)fluoromethyl phenyl and propyl ketones. In the presence of DBU, these compounds react with aldehydes tested to give alpha-fluoroenones with high Z-selectivity. The use of N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfanyl)fluoroacetamide as a common fluorinated intermediate in the synthesis of alpha-fluorovinyl Weinreb amides and alpha-fluoroenones has been demonstrated. Application of the Weinreb amide to alpha-flu-fluoro allyl amine synthesis is also shown. English AMER CHEMICAL SOC HIGH-YIELD SYNTHESIS JULIA OLEFINATION SULFONES DERIVATIVES EFFICIENT HALIDES ROUTE MILD FLUOROOLEFINS ESTERS alpha-Fluorovinyl Weinreb Amides and alpha-Fluoroenones from a Common Fluorinated Building Block Article 10.1021/jo802784w 1 JOURNAL OF ORGANIC CHEMISTRY, v.74, no.10, pp.3689 - 3697 JOURNAL OF ORGANIC CHEMISTRY 74 10 3689 3697 scie scopus 000265991200010 Chemistry, Organic Chemistry Article HIGH-YIELD SYNTHESIS JULIA OLEFINATION SULFONES DERIVATIVES EFFICIENT HALIDES ROUTE MILD FLUOROOLEFINS ESTERS Julia olefination condensation reaction Weinreb amide olefination reaction DBU α-fluorovinyl α-fluoroenone