Cobalt-Catalyzed Enantiospecific Dynamic Kinetic Cross-Electrophile Vinylation of Allylic Alcohols with Vinyl Triflates
Asymmetric cross-electrophile coupling has emerged as a promising tool for producing chiral molecules; however, the potential of this chemistry with metals other than nickel remains unknown. Herein, we report a cobalt-catalyzed enantiospecific vinylation reaction of allylic alcohol with vinyl trifla...
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| Veröffentlicht in: | Journal of the American Chemical Society 2021-10, Vol.143 (39), p.15930-15935 |
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| container_issue | 39 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 143 |
| creator | Ma, Wei-Yuan Han, Guan-Yu Kang, Shaolin Pang, Xiaobo Liu, Xue-Yuan Shu, Xing-Zhong |
| description | Asymmetric cross-electrophile coupling has emerged as a promising tool for producing chiral molecules; however, the potential of this chemistry with metals other than nickel remains unknown. Herein, we report a cobalt-catalyzed enantiospecific vinylation reaction of allylic alcohol with vinyl triflates. This work establishes a new method for the synthesis of enantioenriched 1,4-dienes. The reaction proceeds through a dynamic kinetic coupling approach, which not only allows for direct functionalization of allylic alcohols but also is essential to achieve high chemoselectivity. The use of cobalt enables the reactions to proceed with high enantiospecificity, which have failed to be realized by nickel catalysts. |
| doi_str_mv | 10.1021/jacs.1c08695 |
| format | Article |
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Am. Chem. Soc</addtitle><date>2021-10-06</date><risdate>2021</risdate><volume>143</volume><issue>39</issue><spage>15930</spage><epage>15935</epage><pages>15930-15935</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>Asymmetric cross-electrophile coupling has emerged as a promising tool for producing chiral molecules; however, the potential of this chemistry with metals other than nickel remains unknown. Herein, we report a cobalt-catalyzed enantiospecific vinylation reaction of allylic alcohol with vinyl triflates. This work establishes a new method for the synthesis of enantioenriched 1,4-dienes. The reaction proceeds through a dynamic kinetic coupling approach, which not only allows for direct functionalization of allylic alcohols but also is essential to achieve high chemoselectivity. 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| title | Cobalt-Catalyzed Enantiospecific Dynamic Kinetic Cross-Electrophile Vinylation of Allylic Alcohols with Vinyl Triflates |
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