Issue 39, 2014
From the journal:

Organic & Biomolecular Chemistry

Catalytic amide allylation of α-ketoesters: extremely high enantioselective synthesis of ester functionalised α-methylene-γ-butyrolactones†

Masaki Takahashi,a   Yusuke Murata,b   Masahiro Ishida,a   Fumitoshi Yagishita,c   Masami Sakamoto,c   Tetsuya Sengokua  and  Hidemi Yoda*ab  

* Corresponding authors

a Department of Applied Chemistry, Graduate School of Engineering, Shizuoka University, 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan
E-mail: tchyoda@ipc.shizuoka.ac.jp
Fax: +81 53 478 1150
Tel: +81 53 478 1150

b Graduate School of Science and Technology, Shizuoka University, 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan

c Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

Abstract

This communication reports a significant breakthrough on the novel catalytic amide allylation to the acyclic α-ketoester systems, achieving satisfactorily high yields and extremely high levels of the asymmetric induction to allow for highly enantioselective synthesis of ester functionalised α-methylene-γ-butyrolactones.

Graphical abstract: Catalytic amide allylation of α-ketoesters: extremely high enantioselective synthesis of ester functionalised α-methylene-γ-butyrolactones

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C4OB01508H
Article type
Communication
Submitted
17 Jul 2014
Accepted
12 Aug 2014
First published
12 Aug 2014

Org. Biomol. Chem., 2014,12, 7686-7689

Permissions

Request permissions

Catalytic amide allylation of α-ketoesters: extremely high enantioselective synthesis of ester functionalised α-methylene-γ-butyrolactones

M. Takahashi, Y. Murata, M. Ishida, F. Yagishita, M. Sakamoto, T. Sengoku and H. Yoda, Org. Biomol. Chem., 2014, 12, 7686 DOI: 10.1039/C4OB01508H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements