Asymmetric Bromoaminocyclization and Desymmetrization of Cyclohexa-1,4-dienes through Anion Phase-Transfer Catalysis
Asymmetric Bromoaminocyclization and Desymmetrization of Cyclohexa-1,4-dienes through Anion Phase-Transfer Catalysis
复制标题
阴离子相转移催化环己-1,4-二烯的不对称溴氨基环化和去对称化
DOI：
10.1021/acs.orglett.1c02817
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发表时间：
2021
期刊：
影响因子：
5.2
通讯作者：
Deng Jun
中科院分区：
文献类型：
--
作者：
Long Hai-Jiao;Li Yin-Long;Zhang Bing-Qian;Xiao Wen-Ying;Zhang Xiao-Ying;He Ling;Deng Jun
利用手性阴离子相转移催化剂，实现了前手性环己-1，4-二烯的不对称溴胺环化反应，得到了一系列对映体富集的含全碳四元立构中心的顺式-3a-芳基氢吲哚，产率高达78%，对映体选择性高达97%ee.此外，通过对（+）-Mesembrane的不对称合成，证明了该方法在天然产物全合成中的潜在应用。
The catalytic enantioselective desymmetrizing bromoaminocyclization of prochiral cyclohexa-1,4-dienes has been achieved by using chiral anion phase-transfer catalysis, providing a range of enantioenrichedcis-3a-arylhydroindoles bearing an all-carbon quaternary stereocenter in good yields (up to 78%) and excellent enantioselectivities (up to 97% ee). Furthermore, the potential application of this methodology to natural product total synthesis was demonstrated by the asymmetric synthesis of (+)-Mesembrane.