Issue 25, 2013
From the journal:

Organic & Biomolecular Chemistry

Aniline mediated oxidative C–C bond cleavage of α-alkoxy aldehydes in air and a model reaction for the synthesis of α-(d)-amino acid derivatives†

Bin Hu,a   Yunfeng Li,‡a   Zhongjun Li*a  and  Xiangbao Meng*a  

* Corresponding authors

a State Key Laboratory of Natural and Biomimetic Drugs, Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, PR China
E-mail: zjli@bjmu.edu.cn, xbmeng@bjmu.edu.cn
Fax: +86 10 82805496
Tel: +86 10 82801714

Abstract

A metal-free and 4-methyl aniline mediated method for the oxidative C–C bond cleavage has been developed. The reaction proceeds in air using molecular oxygen as the oxidant, affording one-carbon shortened esters in moderate to good yields within a short time. Moreover, it provides a model reaction for the highly enantioselective synthesis of (D)-serine esters by combining with a L-proline catalyzed Mannich reaction.

Graphical abstract: Aniline mediated oxidative C–C bond cleavage of α-alkoxy aldehydes in air and a model reaction for the synthesis of α-(d)-amino acid derivatives

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C3OB40685G
Article type
Communication
Submitted
05 Apr 2013
Accepted
13 May 2013
First published
14 May 2013

Org. Biomol. Chem., 2013,11, 4138-4141

Permissions

Request permissions

Aniline mediated oxidative C–C bond cleavage of α-alkoxy aldehydes in air and a model reaction for the synthesis of α-(D)-amino acid derivatives

B. Hu, Y. Li, Z. Li and X. Meng, Org. Biomol. Chem., 2013, 11, 4138 DOI: 10.1039/C3OB40685G

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