Pyrrolidine-Mediated Direct Preparation of (E)-Monoarylidene Derivatives of Homo- and Heterocyclic Ketones with Various Aldehydes

Molecules

Xin Gu¹  Xiaoyan Wang²  Fengtian Wang¹  Hongbao Sun¹  Jie Liu¹  Yongmei Xie¹ 

[1] State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, China; E-Mails:;Analytical & Testing Center, Sichuan University, Chengdu 610064, China; E-Mail:

关键词: α;    β-unsaturated ketones;    pyrrolidine;    1-methyl-4-piperidone;    Mannich-elimination sequence;    Claisen-Schmidt condensation;   

DOI  :  10.3390/molecules19021976

来源: mdpi

【 摘 要 】

An efficient method for the facile synthesis of (E)-monoarylidene derivatives of homo- and heterocyclic ketones with various aldehydes in the presence of a pyrrolidine organocatalyst has been achieved. A range of α,β-unsaturated ketones were obtained in moderate to high yields (up to 99%). Unlike the Claisen-Schmidt condensation process, the formation of undesired bisarylidene byproducts is not observed. The possible reaction mechanism suggests that the reaction proceeds via a Mannich-elimination sequence.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.