Cobalt–Bisoxazoline-Catalyzed Asymmetric Kumada Cross-Coupling of Racemic α‑Bromo Esters with Aryl Grignard Reagents
The first cobalt-catalyzed asymmetric Kumada cross-coupling with high enantioselectivity has been developed. The reaction affords a unique strategy for the enantioselective arylation of α-bromo esters catalyzed by a cobalt–bisoxazoline complex. A variety of chiral α-arylalkanoic esters were prepared...
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| Veröffentlicht in: | Journal of the American Chemical Society 2014-12, Vol.136 (50), p.17662-17668 |
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| container_end_page | 17668 |
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| container_issue | 50 |
| container_start_page | 17662 |
| container_title | Journal of the American Chemical Society |
| container_volume | 136 |
| creator | Mao, Jianyou Liu, Feipeng Wang, Min Wu, Lin Zheng, Bing Liu, Shangzhong Zhong, Jiangchun Bian, Qinghua Walsh, Patrick J |
| description | The first cobalt-catalyzed asymmetric Kumada cross-coupling with high enantioselectivity has been developed. The reaction affords a unique strategy for the enantioselective arylation of α-bromo esters catalyzed by a cobalt–bisoxazoline complex. A variety of chiral α-arylalkanoic esters were prepared in excellent enantioselectivity and yield (up to 97% ee and 96% yield). The arylated products were transformed into α-arylcarboxylic acids and primary alcohols without erosion of ee. The new enantioenriched α-arylpropionic esters synthesized herein are potentially useful in the development of nonsteroidal anti-inflammatory drugs. This method was conducted on gram-scale and applied to the synthesis of highly enantioenriched (S)-fenoprofen and (S)-ar-turmerone. |
| doi_str_mv | 10.1021/ja5109084 |
| format | Article |
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The reaction affords a unique strategy for the enantioselective arylation of α-bromo esters catalyzed by a cobalt–bisoxazoline complex. A variety of chiral α-arylalkanoic esters were prepared in excellent enantioselectivity and yield (up to 97% ee and 96% yield). The arylated products were transformed into α-arylcarboxylic acids and primary alcohols without erosion of ee. The new enantioenriched α-arylpropionic esters synthesized herein are potentially useful in the development of nonsteroidal anti-inflammatory drugs. 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Am. Chem. Soc</addtitle><date>2014-12-17</date><risdate>2014</risdate><volume>136</volume><issue>50</issue><spage>17662</spage><epage>17668</epage><pages>17662-17668</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>The first cobalt-catalyzed asymmetric Kumada cross-coupling with high enantioselectivity has been developed. The reaction affords a unique strategy for the enantioselective arylation of α-bromo esters catalyzed by a cobalt–bisoxazoline complex. A variety of chiral α-arylalkanoic esters were prepared in excellent enantioselectivity and yield (up to 97% ee and 96% yield). The arylated products were transformed into α-arylcarboxylic acids and primary alcohols without erosion of ee. The new enantioenriched α-arylpropionic esters synthesized herein are potentially useful in the development of nonsteroidal anti-inflammatory drugs. 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| title | Cobalt–Bisoxazoline-Catalyzed Asymmetric Kumada Cross-Coupling of Racemic α‑Bromo Esters with Aryl Grignard Reagents |
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