TY - JOUR
T1 - Asymmetric Heck reaction-carbanion capture process. Catalytic asymmetric total synthesis of (-)-Δ(9(12))-capnellene
AU - Ohshima, Takashi
AU - Kagechika, Katsuji
AU - Adachi, Midori
AU - Sodeoka, Mikiko
AU - Shibasaki, Masakatsu
PY - 1996/7/31
Y1 - 1996/7/31
N2 - An asymmetric Heck reaction-carbanion capture process was realized for the first time, making possible the catalytic asymmetric synthesis of various functionalized bicyclo[3.3.0]octane derivatives 6 in up to 94% ee. Sodium bromide had interesting effects on this asymmetric Heck reaction-carbanion capture process, and these effects were useful for improving the enantiomeric excess. Furthermore, the catalytic asymmetric synthesis of (-)-Δ(9(12))-capnellene (7) was achieved for the first time, using 6b as a key intermediate and a radical cyclization as a key step.
AB - An asymmetric Heck reaction-carbanion capture process was realized for the first time, making possible the catalytic asymmetric synthesis of various functionalized bicyclo[3.3.0]octane derivatives 6 in up to 94% ee. Sodium bromide had interesting effects on this asymmetric Heck reaction-carbanion capture process, and these effects were useful for improving the enantiomeric excess. Furthermore, the catalytic asymmetric synthesis of (-)-Δ(9(12))-capnellene (7) was achieved for the first time, using 6b as a key intermediate and a radical cyclization as a key step.
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U2 - 10.1021/ja9609359
DO - 10.1021/ja9609359
M3 - Article
AN - SCOPUS:0029773894
SN - 0002-7863
VL - 118
SP - 7108
EP - 7116
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 30
ER -