a-Fluorovinyl Weinreb Amides and a-Fluoroenones from a Commom Fluorinated Building Block
- a-Fluorovinyl Weinreb Amides and a-Fluoroenones from a Commom Fluorinated Building Block
- 아룬 고쉬; 샤이발 바네리; 샤켓 쉬하; 강순방; 바바라 작
- Julia olefination; condensation reaction; Weinreb amide; olefination reaction; DBU; α-fluorovinyl; α-fluoroenone
- Issue Date
- Journal of organic chemistry
- VOL 74, 3689-3697
- 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 R-fluorovinyl Weinreb amides. Olefination reactions proceed under mild, DBUmediated
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 α-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 α-fluorovinyl Weinreb amides and α-fluoroenones has been demonstrated. Application
of the Weinreb amide to α-fluoro allyl amine synthesis is also shown.
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