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Copper‐Catalyzed Stereospecific Hydroboration of Internal Allylic Alcohols
Author(s) -
Ji Enhui,
Meng Haiwen,
Zheng Yue,
Ramadoss Velayudham,
Wang Yahui
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901435
Subject(s) - hydroboration , stereospecificity , chemistry , allylic rearrangement , diastereomer , silylation , organic chemistry , catalysis , ether , silyl ether , medicinal chemistry
An effective Cu‐catalyzed stereospecific hydroboration of aliphatic and aromatic 1,1,2‐trisubstituted internal allylic alcohols has been reported. This reaction proceeds via a silyl ether transient protection of allylic alcohols and subsequent stereospecific hydroboration. Followed by an oxidative workup, an array of acyclic, cyclic, and heterocyclic 1,3‐diols was synthesized in good to excellent yields with good functional group tolerance and excellent diastereomeric ratios (> 20:1).