化学
硅烷化
羟醛反应
分子内力
药物化学
醛
有机化学
催化作用
作者
Aya Nowaki,Mizuki Kawano,Fuka Hori,Yasuro Fuse,Tetsuzo Yoshimura,Jun‐ichi Matsuo
标识
DOI:10.1002/ejoc.202300351
摘要
Abstract β‐Silyl ketones reacted with aldehydes by treatment with KMMDS in the presence of 18‐crown‐6 to give β,γ‐unsaturated ketones accompanied with a skeletal rearrangement. The reactions proceeded by aldol reaction of β‐silyl ketones with aldehydes followed by [1,4]‐Brook rearrangement and intramolecular 1,2‐addition to form cyclopropanol derivatives, in which carbon‐carbon bond cleavage took place to afford β,γ‐unsaturated ketones. The β,γ‐unsaturated ketones were prepared in a one‐pot manner by conjugate addition of silyl anions to α,β‐unsaturated ketones followed by reactions with aldehydes. The Brook rearrangement proceeded with complete inversion of configuration at the carbon center.
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