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
Hauptverfasser: Mao, Jianyou, Liu, Feipeng, Wang, Min, Wu, Lin, Zheng, Bing, Liu, Shangzhong, Zhong, Jiangchun, Bian, Qinghua, Walsh, Patrick J
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja5109084