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Molecules 2014, 19(2), 1976-1989; doi:10.3390/molecules19021976
Article

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

1,†
,
2,†
,
1
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1
,
1,* , 1,*  and 1
1 State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, China 2 Analytical & Testing Center, Sichuan University, Chengdu 610064, China These authors contributed equally to this work.
* Authors to whom correspondence should be addressed.
Received: 18 December 2013 / Revised: 21 January 2014 / Accepted: 26 January 2014 / Published: 12 February 2014
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Abstract

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.
Keywords: α,β-unsaturated ketones; pyrrolidine; 1-methyl-4-piperidone; Mannich-elimination sequence; Claisen-Schmidt condensation α,β-unsaturated ketones; pyrrolidine; 1-methyl-4-piperidone; Mannich-elimination sequence; Claisen-Schmidt condensation
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Gu, X.; Wang, X.; Wang, F.; Sun, H.; Liu, J.; Xie, Y.; Xiang, M. Pyrrolidine-Mediated Direct Preparation of (E)-Monoarylidene Derivatives of Homo- and Heterocyclic Ketones with Various Aldehydes. Molecules 2014, 19, 1976-1989.

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