- Synthetic studies towards N-substituted 3-vinyl-4-piperidineacetic acid derivatives
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The synthesis and full characterization of two new (E)-2-butenyl)-5-amino-2-pentenoates, (Z)-4-[N-(3-buten-1-yl)benzamido]-2-buten-1-ol, and (Z)-1-chloro-4-[N-(3-buten-l-yl)benzamido]-2-butene are reported. These were designed as substrates for a projected thermal ene cyclization leading to the N-substituted 3-vinyl-4-piperidineacetic acid scaffold. Although conditions for this ene-cyclization have not yet been uncovered, the ease of preparation of these ene-cyclization substrates gives promise for their future use.
- Johnson, David A.,Gribble, Gordon W.
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p. 178 - 195
(2019/05/15)
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- β-NITROGENATED RADICALS IN ORGANIC SYNTHESIS: REACTIONS WITH ELECTROPHILIC OLEFINS
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The reaction of iodoamide 1a or iodocarbamates 1b,c with electrophilic olefins 2a-e and in situ generated tributyltin hydride (from tributyltin chloride in a substoichiometric amout and an excess of sodium borohydride) in the presence of a catalytic amount of AIBN in dry ethanol at 0 to 20 deg C yields, after treatment with aqueous sodium fluoride, the expected coupling products 3aa-ce in moderate yields.Compounds 4a-c resulting from an iodine/hydrogen exchange in the starting materials 1a-c are also obtained as by-products in variable amounts.Parablas Clave: radicales β-funcionalizados, yodoamidas, formacion de enlaces C-C
- Foubelo, Francisco,Lloret, Francisco,Yus, Miguel
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p. 260 - 266
(2007/10/03)
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