TY - JOUR
T1 - Control of chemoselectivity in dirhodium(II)-catalyzed reaction of 5,6- dioxygenated 2-diazo-3-oxohexanoates
T2 - C-H insertion reaction versus oxonium ylide formation
AU - Yakura, Takayuki
AU - Ueki, Akiharu
AU - Morioka, Yukiko
AU - Kurata, Toyoshige
AU - Tanaka, Kenji
AU - Ikeda, Masazumi
PY - 1998
Y1 - 1998
N2 - Methyl (S)-2-diazo-4-(3,3-dimethyl-2,4-dioxolan-1-yl)-3-oxobutanoate (1), upon treatment with Rh2(OAc)4 in boiling dichloromethane, gave methyl (1S,5S)-2,2-dimethyl-7-oxo-3,8-dioxabicyclo[3,2.1]octane-1-carboxylate (2) via oxonium ylide formation/1,2-shift. On the other hand, similar treatment of methyl (S)-5,6-bis(tertbutyldimethylsilyloxy)-2-diazo-3-oxohexanoate (3a) gave methyl 3-(tert-butyldimethylsilyloxy)-5-oxo-1-cyclopentene-1-carboxylate (4a) via the C-H insertion reaction.
AB - Methyl (S)-2-diazo-4-(3,3-dimethyl-2,4-dioxolan-1-yl)-3-oxobutanoate (1), upon treatment with Rh2(OAc)4 in boiling dichloromethane, gave methyl (1S,5S)-2,2-dimethyl-7-oxo-3,8-dioxabicyclo[3,2.1]octane-1-carboxylate (2) via oxonium ylide formation/1,2-shift. On the other hand, similar treatment of methyl (S)-5,6-bis(tertbutyldimethylsilyloxy)-2-diazo-3-oxohexanoate (3a) gave methyl 3-(tert-butyldimethylsilyloxy)-5-oxo-1-cyclopentene-1-carboxylate (4a) via the C-H insertion reaction.
KW - 1,2-shift
KW - C-H insertion reaction
KW - Cyclopentenone
KW - Diazoketone
KW - Dirhodium(II) catalyst
KW - Oxonium ylide
UR - http://www.scopus.com/inward/record.url?scp=0031827988&partnerID=8YFLogxK
U2 - 10.1248/cpb.46.1182
DO - 10.1248/cpb.46.1182
M3 - 学術論文
AN - SCOPUS:0031827988
SN - 0009-2363
VL - 46
SP - 1182
EP - 1183
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
IS - 7
ER -