4.6 Article

Alkylative Carboxylation of Ynamides and Allenamides with Functionalized Alkylzinc Halides and Carbon Dioxide by a Copper Catalyst

期刊

CHEMISTRY-A EUROPEAN JOURNAL
卷 25, 期 35, 页码 8363-8370

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201901153

关键词

allenamides; carbon dioxide; carboxylation; copper; ynamides

资金

  1. JSPS [17H06451, 17K08232]
  2. Grants-in-Aid for Scientific Research [17K08232, 17H06451] Funding Source: KAKEN

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The alkylative carboxylation of ynamides and allenamides with CO2 and alkylzinc halides catalyzed by a copper catalyst was developed. A variety of alkylzinc halides bearing functional groups were used for this transformation to afford alpha,beta-unsaturated carboxylic acids, which contain the alpha,beta-dehydroamino acid skeleton, introducing the corresponding alkyl group and CO2 across the carbon-carbon triple or double bond. This alkylative carboxylation formally consists of Cu-catalyzed carbozincation of ynamides or allenamides with alkylzinc halides and the subsequent nucleophilic carboxylation of the resulting alkenylzinc species with CO2. This protocol would be a useful method for the synthesis of alpha,beta-dehydroamino acid derivatives possessing a functionalized alkyl group due to the high regio- and stereoselectivity, simple one-pot procedure as well as the use of CO2 as a starting material.

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