Stereoselective synthesis of methyl (Z)-(4,4-difluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylidene)acetate using a dianion Horner-Wadsworth-Emmons reagent.
Stereoselective synthesis of methyl (Z)-(4,4-difluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylidene)acetate (1a) is described. Z-selectivity of the Horner-Wadsworth-Emmons (HWE) reaction was obtained based on an investigation of the reaction conditions for introduction of a methylidene group onto the 5-position of benzazepine.
Shimada
Yoshiaki
Y
Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka, Tsukuba, Ibaraki 305-8585, Japan. shimada@yamanouchi.co.jp
Akane
Hiroaki
H
Taniguchi
Nobuaki
N
Matsuhisa
Akira
A
Kawano
Noriyuki
N
Tanaka
Akihiro
A
D000085:Acetates; D001552:Benzazepines / Q000032:analysis* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013678:Technology, Pharmaceutical / Q000379:methods*
D000085:Acetates; D001552:Benzazepines