TY - JOUR
T1 - Effect of amines on the selective bromination of some β-substituted-2- butenoic esters
AU - Nakada, Masahisa
AU - Kojima, Ei Ichi
AU - Ichinose, Hidehiro
N1 - Funding Information:
Acknowledgement. : We are indebted to the Hightech Research Center Project (Ministry of Education, Science, Sports and Culture) for financial support.
PY - 2000
Y1 - 2000
N2 - The effect of amines on the selective bromination of some β- substituted-2-butenoic esters is described. The bromination of methyl (Z)4-t- butyldiphenylsilyloxy-3-methylbutenoate 2 in the presence of DIPEA (N, N- diisopropylethylamine) and the successive treatment of the obtained dibromide with potassium t-butoxide afford the desired Z bromide selectively. But the corresponding E bromide forms exclusively when 2, 6-di-t-butyl-4- methylpyridine is used in the bromination.
AB - The effect of amines on the selective bromination of some β- substituted-2-butenoic esters is described. The bromination of methyl (Z)4-t- butyldiphenylsilyloxy-3-methylbutenoate 2 in the presence of DIPEA (N, N- diisopropylethylamine) and the successive treatment of the obtained dibromide with potassium t-butoxide afford the desired Z bromide selectively. But the corresponding E bromide forms exclusively when 2, 6-di-t-butyl-4- methylpyridine is used in the bromination.
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U2 - 10.1080/00397910008087098
DO - 10.1080/00397910008087098
M3 - Article
AN - SCOPUS:0034062233
SN - 0039-7911
VL - 30
SP - 863
EP - 868
JO - Synthetic Communications
JF - Synthetic Communications
IS - 5
ER -