Our official English website, www.x-mol.net, welcomes your
feedback! (Note: you will need to create a separate account there.)
Synthesis of 8-Oxabicyclo[3.2.1]octanes by TiCl4-Mediated Reactions of 3-Alkoxycyclobutanones and Allenylsilanes
Synlett ( IF 1.7 ) Pub Date : 2018-10-29 , DOI: 10.1055/s-0037-1611276 Jun-ichi Matsuo 1 , Tatsuo Onnagawa , Mizuki Yamazaki , Tomoyuki Yoshimura
Synlett ( IF 1.7 ) Pub Date : 2018-10-29 , DOI: 10.1055/s-0037-1611276 Jun-ichi Matsuo 1 , Tatsuo Onnagawa , Mizuki Yamazaki , Tomoyuki Yoshimura
Affiliation
|
1-Substituted allenylsilanes reacted with 3-alkoxycyclobutanones in the presence of TiCl4 to afford 8-oxabicyclo[3.2.1]octan-3-ones stereoselectively. Nucleophilic attack of allenylsilanes to a 1,4-zwitterionic intermediate formed from 3-alkoxycyclobutanones and TiCl4 followed by 1,2-silyl migration, five-membered cyclization with an alkoxy group, and seven-membered cyclization of titanium enolate was proposed. Deuteration and one-pot Peterson olefination suggested that alkyl titanium species were formed after cyclization to 8-oxabicyclo[3.2.1]octane skeletons.
中文翻译：
通过 TiCl4 介导的 3-烷氧基环丁酮和艾伦基硅烷的反应合成 8-氧杂双环 [3.2.1] 辛烷
1-取代的烯丙基硅烷在 TiCl4 存在下与 3-烷氧基环丁酮反应，立体选择性地得到 8-氧杂双环[3.2.1]辛烷-3-酮。提出了烯基硅烷对由 3-烷氧基环丁酮和 TiCl4 形成的 1,4-两性离子中间体的亲核攻击，然后是 1,2-甲硅烷基迁移、具有烷氧基的五元环化和烯醇钛的七元环化。氘化和一锅 Peterson 烯化表明在环化为 8-氧杂双环 [3.2.1] 辛烷骨架后形成了烷基钛物种。
更新日期：2018-10-29
中文翻译：
通过 TiCl4 介导的 3-烷氧基环丁酮和艾伦基硅烷的反应合成 8-氧杂双环 [3.2.1] 辛烷
1-取代的烯丙基硅烷在 TiCl4 存在下与 3-烷氧基环丁酮反应，立体选择性地得到 8-氧杂双环[3.2.1]辛烷-3-酮。提出了烯基硅烷对由 3-烷氧基环丁酮和 TiCl4 形成的 1,4-两性离子中间体的亲核攻击，然后是 1,2-甲硅烷基迁移、具有烷氧基的五元环化和烯醇钛的七元环化。氘化和一锅 Peterson 烯化表明在环化为 8-氧杂双环 [3.2.1] 辛烷骨架后形成了烷基钛物种。
京公网安备 11010802027423号