Asymmetric Bromoaminocyclization and Desymmetrization of Cyclohexa-1,4-dienes through Anion Phase-Transfer Catalysis
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 enantioenriched cis-3a-arylhydroindoles bearing an all-carbon quaternary stereocenter in good yields (up to 78%...
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| Veröffentlicht in: | Organic letters 2021-11, Vol.23 (21), p.8153-8157 |
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| container_issue | 21 |
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| container_title | Organic letters |
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| creator | Long, Hai-Jiao Li, Yin-Long Zhang, Bing-Qian Xiao, Wen-Ying Zhang, Xiao-Ying He, Ling Deng, Jun |
| description | 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 enantioenriched cis-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. |
| doi_str_mv | 10.1021/acs.orglett.1c02817 |
| format | Article |
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Lett</addtitle><description>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 enantioenriched cis-3a-arylhydroindoles bearing an all-carbon quaternary stereocenter in good yields (up to 78%) and excellent enantioselectivities (up to 97% ee). 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Lett</addtitle><date>2021-11-05</date><risdate>2021</risdate><volume>23</volume><issue>21</issue><spage>8153</spage><epage>8157</epage><pages>8153-8157</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>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 enantioenriched cis-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.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>34623166</pmid><doi>10.1021/acs.orglett.1c02817</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-6547-0244</orcidid></addata></record> |
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| title | Asymmetric Bromoaminocyclization and Desymmetrization of Cyclohexa-1,4-dienes through Anion Phase-Transfer Catalysis |
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