Issue 72, 2014

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

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

Supplementary files

Article information

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

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

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