Synthesis of gem-Difluoromethylene Building Blocks through Regioselective Allylation of gem-Difluorocyclopropanes

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• 作者：Daisuke Munemori ; Kent Narita ; Toshiki Nokami ; Toshiyuki Itoh
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：May 16, 2014
• 年：2014
• 卷：16
• 期：10
• 页码：2638-2641
• 全文大小：255K
• 年卷期：v.16,no.10(May 16, 2014)
• ISSN：1523-7052

文摘

gem-Difluorocyclopropane derivatives react with allyltributylstannane in the presence of 2,2鈥?azobis(isobutyronitrile) to afford 1,6-dienes with a gem-difluoromethylene moiety at the allylic position. The reaction proceeds regioselectively with high yields, and the 1,6-dinenes obtained are good precursors for cyclic systems containing a gem-difluoromethylene moiety. Although S-methyl carbonodithioate also works as a leaving group, rearrangement of the leaving group competes with the desired allylation, depending on the amount of allyltributylstannane.