Stereoselective Dehydroxyboration of Allylic Alcohols to Access (E)-Allylboronates by a Combination of C–OH Cleavage and Boron Transfer under Iron Catalysis,Organic Letters

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Stereoselective Dehydroxyboration of Allylic Alcohols to Access (E)-Allylboronates by a Combination of C–OH Cleavage and Boron Transfer under Iron Catalysis
Organic Letters ( IF 4.9 ) Pub Date : 2021-11-15 , DOI: 10.1021/acs.orglett.1c03359
Wei Su ₁ , Ting-Ting Wang ₁ , Xia Tian ₁ , Jian-Rong Han ₁ , Xiao-Li Zhen ₁ , Shi-Ming Fan ₂ , Ya-Xin You ₁ , Yu-Kun Zhang ₁ , Rui-Xiao Qiao ₂ , Qiushi Cheng _{1,

3} , Shouxin Liu ₂

Affiliation

Iron-catalyzed direct S_N2′ dehydroxyboration of allylic alcohols has been developed to access (E)-stereoselective allylboronates. Allylic alcohols with diverse structures and functional groups, especially derived from natural products, underwent smooth transformation. The six-membered ring transition state formed by allylic alcohols and iron–boron intermediate was indicated to be the key component involved in transfer of the boron group, activation of the C–OH bond, and control of the stereoselectivity.

中文翻译：

铁催化下 C-OH 裂解和硼转移相结合的烯丙醇立体选择性脱羟基硼酸制备 (E)-烯丙基硼酸酯

铁催化的烯丙醇直接 S _N 2' 脱羟基硼酸已被开发用于获得 ( E )-立体选择性烯丙基硼酸酯。具有多种结构和官能团的烯丙醇，特别是来自天然产物的烯丙醇，经历了平稳的转变。由烯丙醇和铁-硼中间体形成的六元环过渡态被证明是参与硼基团转移、C-OH键活化和立体选择性控制的关键成分。

更新日期：2021-12-03

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