TY - JOUR
T1 - Functional desymmetrization of 1,3-dioximes for the obtention of 1,2,3-hetero trisubstituted carbocycles
AU - Lobo, Ana Maria Félix Trindade
AU - Prabhakar, Alberto Sundaresan
PY - 2010/1/1
Y1 - 2010/1/1
N2 - Carbocylic 1,3-dioximes react with acyl chlorides giving systems that may, upon heating, suffer [3,3]-sigmatropic rearrangements in high yields in only one of the oximes esters, yielding 1,3-dinitrogen-2-oxygen trisubstituted carbocycles. Use of more reactive electrophiles, such as p-toluenesulfonyl chloride and diethyl chlorophosphate, introduces the halogen at position 2, while cleaving the N-O bond of just one of the oxime functions. (C) 2010 Elsevier Ltd. All rights reserved.
AB - Carbocylic 1,3-dioximes react with acyl chlorides giving systems that may, upon heating, suffer [3,3]-sigmatropic rearrangements in high yields in only one of the oximes esters, yielding 1,3-dinitrogen-2-oxygen trisubstituted carbocycles. Use of more reactive electrophiles, such as p-toluenesulfonyl chloride and diethyl chlorophosphate, introduces the halogen at position 2, while cleaving the N-O bond of just one of the oxime functions. (C) 2010 Elsevier Ltd. All rights reserved.
KW - Oximes Sigmatropic rearrangements Carbocycles Amines Esters oseltamivir phosphate tamiflu 3
KW - 3-sigmatropic rearrangements acid oximes
U2 - 10.1016/j.tetlet.2010.02.048
DO - 10.1016/j.tetlet.2010.02.048
M3 - Article
SN - 0040-4039
VL - 51
SP - 2029
EP - 2031
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 15
ER -