四取代硼酸盐的1,2-氧迁移反应在环醚合成中的应用  

The construction of cyclic ethers via a 1,2-oxygen migration reaction of boron ate-complex

作　　者：郑开敏 杨民 刘锟 黄娴 韩丛丛 杨刚 何述钟 ZHENG Kai-min;YANG Min;LIU Kun;HUANG Xian;HAN Cong-cong;YANG Gang;HE Shu-zhong(School of Pharmaceutical Sciences,Guizhou University,Guiyang 550025,China;School of Pharmaceutical Sciences,Guizhou University,Guizhou Engineering Laboratory for Synthetic Drugs,Guiyang 550025,China)

机构地区：[1]贵州大学药学院,贵州贵阳550025 [2]贵州大学药学院贵州省药物合成工程实验室,贵州贵阳550025

出　　处：《化学研究与应用》2018年第7期1100-1105,共6页Chemical Research and Application

基　　金：国家自然科学基金地区项目(21562011)资助;贵州省科学技术基金项目(黔科合J字[2015]2047号)资助

摘　　要：本文应用四取代硼酸盐(boron ate-complex)分子内1,2氧迁移反应合成环醚。在本反应中,含羰基的有机硼烷在碱的作用下发生分子内亲核反应构建boron ate-complex,然后该复合物发生两次1,2氧迁移反应合成环醚。该方法反应时间短、条件温和、收率高且不需任何催化剂,另一方面为构建碳-氧杂环提供了新方法,本文应用该方法完成了苯基-(2-四氢呋喃)甲酮和苯基-(2-四氢-2H-吡喃)甲酮的合成。A new method for the synthesis of cyclic ethers via 1,2-O-migration of boron ate-complex was establish-ed.Using carbonyl containing boron compounds as the substrates,LDA induced enolate formation followed by in-tramolecular addition with boron provided boron ate-complex intermediates.These intermediates underwent a quickly 1,2-O-migration initiated reaction sequence to furnish cyclic ethers.The reaction provided a mild and effective method for the construction of O-heterocyclic compounds.Based on this reaction,phenyl（ tetrahydrofuran-2-yl） methanone and phenyl（ tetrahydro-2 H-pyran-2-yl） methanone were successfuly synthesized with good yields.

关 键 词：BORON ate-complex 1 2-氧迁移反应 环醚 

分 类 号：O623.84[理学—有机化学]