Highly Efficient and Regioselective Synthesis of N‐Acyl Protected 2‐Aminoacrylates through a PPh3‐Catalyzed Reaction of Alkyl Propiolates with Amides

Author:

Wang Kaikai1ORCID,Li Yanli2,Pan Pengtao2,Zhou Nan1,He Xiaolong3,Chen Rongxiang1ORCID

Affiliation:

1. School of Pharmacy Xinxiang University Xinxiang Henan 453000 China.

2. Medical College Xinxiang University Xinxiang Henan 453000 China

3. School of Food and Bioengineering Xihua University Chengdu 610039

Abstract

AbstractA simple and convenient strategy for the synthesis of N‐acyl protected 2‐aminoacrylates via PPh3‐catalyzed reaction of alkyl propiolates with amides has been developed. This protocol is rapid and highly regioselective to provide various N‐acyl protected 2‐aminoacrylates in high yields (up to 95 %). The chemical structure of the product was determined by X‐ray single‐crystal structure analysis. In contrast, 3‐sulfonamidoacrylates were obtained by Cs2CO3‐catalyzed reactions of alkyl propiolates with secondary sulfamides. Moreover, synthetic utility of this method was further highlighted in the late‐stage modification of drug molecules.

Funder

National Natural Science Foundation of China

Department of Science and Technology of Sichuan Province

Publisher

Wiley

Subject

General Chemistry

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