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Cobalt-bisoxazoline-catalyzed Asymmetric Kumada Cross-Coupling of Racemic α-bromo Esters With Aryl Grignard Reagents

Cobalt-bisoxazoline-catalyzed Asymmetric Kumada Cross-Coupling of Racemic α-bromo Esters With Aryl Grignard Reagents

Jianyou Mao, Feipeng Liu, Min Wang, Lin Wu, Bing Zheng, Shangzhong Liu, Jiangchun Zhong, Qinghua Bian, Patrick J Walsh

J Am Chem Soc. 2014 Dec 17;136(50):17662-8.

PMID: 25479180

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. This method was conducted on gram-scale and applied to the synthesis of highly enantioenriched (S)-fenoprofen and (S)-ar-turmerone.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP532650	(S)-ar-Turmerone		532-65-0	Price

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