TY - JOUR
T1 - Benzotriazole-mediated alkoxyalkylation and acyloxyalkylation
AU - Katritzky, Alan R.
AU - Abdel-Fattah, Ashraf A.A.
AU - Idzik, Krzysztof R.
AU - El-Gendy, Bahaa El Dien M.
AU - Soloducho, Jadwiga
PY - 2007/7/9
Y1 - 2007/7/9
N2 - Reactions of readily available and stable 1-(α-alkoxyalkyl)benzotriazoles type 9a,b and 10a-d with a variety of silyl enol ethers 11 or 1,3-dicarbonyl compounds 13 give the expected ketones 12a-l (60-92%), β-keto esters 14a,b (62-67%), and malonates 14c,d (79-88%) in which a tetrahydrofuran or tetrahydropyran moiety has been introduced at the α position. 1-(Benzotriazol-1-yl)alkyl esters 7 are converted by cyanide anion into cyanohydrin esters 15a-i (55-98%).
AB - Reactions of readily available and stable 1-(α-alkoxyalkyl)benzotriazoles type 9a,b and 10a-d with a variety of silyl enol ethers 11 or 1,3-dicarbonyl compounds 13 give the expected ketones 12a-l (60-92%), β-keto esters 14a,b (62-67%), and malonates 14c,d (79-88%) in which a tetrahydrofuran or tetrahydropyran moiety has been introduced at the α position. 1-(Benzotriazol-1-yl)alkyl esters 7 are converted by cyanide anion into cyanohydrin esters 15a-i (55-98%).
UR - http://www.scopus.com/inward/record.url?scp=34249276739&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2007.04.021
DO - 10.1016/j.tet.2007.04.021
M3 - Article
AN - SCOPUS:34249276739
SN - 0040-4020
VL - 63
SP - 6477
EP - 6484
JO - Tetrahedron
JF - Tetrahedron
IS - 28
ER -