Chen Jiajia, Joseph Devaneyan, Xia Yuanzhi, Lee Sunwoo
Department of Chemistry Chonnam National University, Gwangju 61186, Republic of Korea.
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035, People's Republic of China.
J Org Chem. 2021 Apr 16;86(8):5943-5953. doi: 10.1021/acs.joc.0c02868. Epub 2021 Mar 1.
Activated primary, secondary, and tertiary amides were coupled with enolizable esters in the presence of LiHMDS to obtain good yields of β-ketoesters at room temperature. Notably, this protocol provides an efficient, mild, and high chemoselectivity method to synthesis of β-alkylketoesters using the cross-coupling between aliphatic amides and esters. Meanwhile, gram-scale secondary and primary amides reacted via in situ generated activated tertiary amides and exhibited good reactivity when coupled with esters.
在LiHMDS存在下，活化的伯、仲和叔酰胺与可烯醇化的酯偶联，在室温下获得了高产率的β-酮酯。值得注意的是，该方法提供了一种高效、温和且具有高化学选择性的方法，用于通过脂肪族酰胺与酯之间的交叉偶联合成β-烷基酮酯。同时，克级规模的仲酰胺和伯酰胺通过原位生成的活化叔酰胺进行反应，并且在与酯偶联时表现出良好的反应活性。
