Issue 6, 2005
From the journal:

Organic & Biomolecular Chemistry

Zinc-mediated carbon radical addition to glyoxylic imines in aqueous media for the synthesis of α-amino acids

Masafumi Ueda,a   Hideto Miyabe,b   Hisako Suginoa  and  Takeaki Naito*a  

* Corresponding authors

a Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe, Japan
E-mail: taknaito@kobepharma-u.ac.jp

b Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto, Japan

Abstract

The addition of carbon radicals to glyoxylic imines was studied using zinc dust as a radical initiator. The zinc-mediated radical reaction of glyoxylic oxime ethers and hydrazones proceeded smoothly to give the alkylated products via a carbon–carbon bond-forming process in aqueous media. The reaction of the oxime ethers and hydrazones having an Oppolzer's camphorsultam group provided the corresponding alkylated products, which could be converted into enantiomerically pure α-amino acids. The diastereoselectivities observed in the reaction of hydrazones were better than those obtained in the reaction of oxime ethers.

Graphical abstract: Zinc-mediated carbon radical addition to glyoxylic imines in aqueous media for the synthesis of α-amino acids

About
Cited by
Related
Download options Please wait...

Article information

DOI
https://doi.org/10.1039/B418726A
Article type
Paper
Submitted
13 Dec 2004
Accepted
02 Feb 2005
First published
21 Feb 2005

Org. Biomol. Chem., 2005,3, 1124-1128

Permissions

Request permissions

Zinc-mediated carbon radical addition to glyoxylic imines in aqueous media for the synthesis of α-amino acids

M. Ueda, H. Miyabe, H. Sugino and T. Naito, Org. Biomol. Chem., 2005, 3, 1124 DOI: 10.1039/B418726A

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