E-Selective N-heterocyclic carbene-catalyzed reaction of aldehydes and butadienoates: effect of water and chloroform as the proton shuttle-Reference-Cited by-同舟云学术

E-Selective N-heterocyclic carbene-catalyzed reaction of aldehydes and butadienoates: effect of water and chloroform as the proton shuttle

Published:2018 Issue:17 Volume:5 Page:2560-2567
ISSN:2052-4129
Container-title:Organic Chemistry Frontiers
language:en
Short-container-title:Org. Chem. Front.

Author:

Ma Dengke¹²³⁴⁵,Song Yulong¹²³⁴⁵,Fu Chunling¹²³⁴⁵,Zhang Fang⁶⁷⁸⁹⁵,Guo Yinlong⁶⁷⁸⁹⁵,Huang Xin¹²³⁴⁵,Ma Shengming¹²³⁴⁵^ORCID

Affiliation:

1. Laboratory of Molecular Recognition and Synthesis

2. Department of Chemistry

3. Zhejiang University

4. Hangzhou 310027

5. P. R. China

6. State Key Laboratory of Organometallic Chemistry and National Center for Organic Mass Spectrometry in Shanghai

7. Shanghai Institute of Organic Chemistry

8. Chinese Academy of Sciences

9. Shanghai 200032

Abstract

An N-heterocyclic carbene-catalyzed reaction of aldehydes and butadienoates affording (E)-4-oxo-2-butenoates highly stereoselectively has been developed. Some key intermediates have been detected by an MS study.

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2018/QO/C8QO00579F

Reference57 articles.

1. On the Mechanism of Thiamine Action. IV.1 Evidence from Studies on Model Systems

2. Organocatalysis by N-Heterocyclic Carbenes

3. Carbene Catalysts

4. Extending NHC-Catalysis: Coupling Aldehydes with Unconventional Reaction Partners

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