Reaction of Donor-Acceptor α-Diazo Esters and N, N-Dimethylformamide/γ-Lactams To Generate α-Amino-α-aroylethanoates

Xiaonan Mu; Yulong Niu; Minhui Guan; Hao Chen; Chuan-Ying Li; Lei Wang

doi:10.1021/acs.orglett.4c03771

Reaction of Donor-Acceptor α-Diazo Esters and N, N-Dimethylformamide/γ-Lactams To Generate α-Amino-α-aroylethanoates

Org Lett. 2025 Jan 13. doi: 10.1021/acs.orglett.4c03771. Online ahead of print.

Authors

Xiaonan Mu^{1

2}, Yulong Niu¹, Minhui Guan¹, Hao Chen¹, Chuan-Ying Li², Lei Wang^{1

3}

Affiliations

¹ Advanced Research Institute and Department of Pharmaceutical Sciences, Taizhou University, Taizhou, Zhejiang 318000, People's Republic of China.
² Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou, Zhejiang 310018, People's Republic of China.
³ College of Material Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou, Zhejiang 311121, People's Republic of China.

PMID: 39805131
DOI: 10.1021/acs.orglett.4c03771

Abstract

Herein, we present a metal-free, concise, and efficient protocol for the intermolecular reaction of amides (lactams) with donor-acceptor α-diazo esters to afford the functionalized α-amino-α-aroylethanoates. N-Methyl-2-pyrrolidone (NMP) and N,N-dimethylformamide (DMF) are employed as both reagents and solvents, allowing for the incorporation of all units into the products. The reaction is processed by the ester group migration and compatible with a broad range of substrates up to 50 examples.