Remote Enantioselective [4 + 1] Annulation with Copper-Vinylvinylidene Intermediates
The first copper-catalyzed enantioselective [4 + 1] annulation of yne-allylic esters with 1,3-dicarbonyl compounds was realized through an elegant remote stereocontrol strategy. The very remote ε regioselective nucleophilic substitution was developed by employing a novel chiral copper-vinylvinyliden...
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| Veröffentlicht in: | Journal of the American Chemical Society 2022-11, Vol.144 (46), p.21347-21355 |
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| container_issue | 46 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 144 |
| creator | Kong, Han-Han Zhu, Cuiju Deng, Shuang Xu, Guang Zhao, Ruinan Yao, Chaochao Xiang, Hua-Ming Zhao, Chunhui Qi, Xiaotian Xu, Hao |
| description | The first copper-catalyzed enantioselective [4 + 1] annulation of yne-allylic esters with 1,3-dicarbonyl compounds was realized through an elegant remote stereocontrol strategy. The very remote ε regioselective nucleophilic substitution was developed by employing a novel chiral copper-vinylvinylidene species from the new C4 synthon yne-allylic esters. Thus, greatly diverse spirocycles were obtained with ample scope and excellent levels of chemo-, regio-, and enantioselectivities. Moreover, detailed mechanistic studies suggest an yne-allylic substitution and Conia-ene cascade pathway on the remote stereochemical induction progress. |
| doi_str_mv | 10.1021/jacs.2c09572 |
| format | Article |
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Am. Chem. Soc</addtitle><date>2022-11-23</date><risdate>2022</risdate><volume>144</volume><issue>46</issue><spage>21347</spage><epage>21355</epage><pages>21347-21355</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>The first copper-catalyzed enantioselective [4 + 1] annulation of yne-allylic esters with 1,3-dicarbonyl compounds was realized through an elegant remote stereocontrol strategy. The very remote ε regioselective nucleophilic substitution was developed by employing a novel chiral copper-vinylvinylidene species from the new C4 synthon yne-allylic esters. Thus, greatly diverse spirocycles were obtained with ample scope and excellent levels of chemo-, regio-, and enantioselectivities. 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| source | ACS Publications |
| title | Remote Enantioselective [4 + 1] Annulation with Copper-Vinylvinylidene Intermediates |
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