Synthesis of Multi-Substituted Cyclobutanes and Alkylidenecyclobutanes by the Reaction of Cyclobutylmagnesium Carbenoids with Nucleophiles
作者:Tsuyoshi Satoh、Takashi Kasuya、Masashi Ishigaki、Mio Inumaru、Toshifumi Miyagawa、Nobuhito Nakaya、Shimpei Sugiyama
DOI:10.1055/s-0030-1258391
日期:2011.2
with several nucleophiles to give multi-substituted cyclobutanes. The reaction of the cyclobutylmagnesium carbenoids with lithium α-sulfonyl carbanions afforded alkylidenecyclobutanes in moderate to good yields. cyclobutane - alkylidenecyclobutane - magnesium carbenoid - cyclobutylmagnesium carbenoid - cyclobutylmagnesium chloride
用格氏试剂如乙基镁氯化物,异丙基氯化镁和环戊基氯化镁在THF中低温处理1-氯环丁基对甲苯基亚砜,可高收率得到环丁基镁类化合物。发现生成的镁类胡萝卜素在-78℃下稳定至少30分钟。环丁基镁类化合物与几种亲核试剂反应生成多取代的环丁烷。环丁基镁类胡萝卜素与α-磺酰基碳酸锂的反应以中等至良好的产率提供了亚烷基环丁烷。 环丁烷-亚烷基环丁烷-镁类胡萝卜素-环丁基镁类胡萝卜素-环丁基氯化镁