The Pyrrolidine‐Catalyzed Three‐Component Reactions of Azlactones,N,O‐Acetals and Alcohols: One‐Pot Synthesis of α,β‐Diamino Esters

Author:

Hu Haipeng1ORCID,Wu Xin2,Wang Beining1,Zhao Liuying1,Wang Junyu1,Jiang Zhiyu1

Affiliation:

1. College of Science Sichuan Agricultural University Ya'an Sichuan 625014 People's Republic of China

2. Sichuan Normal University Chengdu Sichuan 610068 People's Republic of China

Abstract

AbstractA pyrrolidine‐catalyzed three‐component reaction of azlactone,N,O‐acetal and alcohol for the synthesis of α,β‐diamino ester was reported. TheN,O‐acetal served as the imine equivalent to occur Mannich reaction with azlactone, and the in situ generated α‐functionalized azlactone subsequently underwent a ring‐opening process in the presence of alcohol. A series of α,β‐diamino esters were obtained in 36–99% yields under mild reaction conditions. The product could be synthesized on gram‐scale and transformed into the α,β‐diamino acid.

Funder

Department of Science and Technology of Sichuan Province

Sichuan Agricultural University

Publisher

Wiley

Subject

General Chemistry

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