Issue 72, 2014
From the journal:

Chemical Communications

The stereoselective synthesis of α-amino aldols starting from terminal alkynes†‡

Tomoya Miura,*a   Takayuki Nakamuro,a   Kentaro Hiragaa  and  Masahiro Murakami*a  

* Corresponding authors

a Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan
E-mail: tmiura@sbchem.kyoto-u.ac.jp, murakami@sbchem.kyoto-u.ac.jp
Fax: +81 75 383 2748

Abstract

A new procedure for the stereoselective synthesis of syn α-amino β-oxy ketones is reported. It consists of two steps; in the first step, α-amino silyl enol ethers having a (Z) geometry are prepared from 1-alkynes via 1-sulfonyl-1,2,3-triazoles. In the second step, the silyl enol ethers undergo the TiCl4-mediated Mukaiyama aldol reaction with aldehydes to produce α-amino β-oxy ketones with excellent syn-selectivity.

Graphical abstract: The stereoselective synthesis of α-amino aldols starting from terminal alkynes

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C4CC04786A
Article type
Communication
Submitted
24 Jun 2014
Accepted
18 Jul 2014
First published
18 Jul 2014

Chem. Commun., 2014,50, 10474-10477

Author version available

Download author version (PDF)

Permissions

Request permissions

The stereoselective synthesis of α-amino aldols starting from terminal alkynes

T. Miura, T. Nakamuro, K. Hiraga and M. Murakami, Chem. Commun., 2014, 50, 10474 DOI: 10.1039/C4CC04786A

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