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Issue 72, 2014
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The stereoselective synthesis of α-amino aldols starting from terminal alkynes

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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

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Publication details

The article was received on 24 Jun 2014, accepted on 18 Jul 2014 and first published on 18 Jul 2014


Article type: Communication
DOI: 10.1039/C4CC04786A
Author version available: Download Author version (PDF)
Citation: Chem. Commun., 2014,50, 10474-10477
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    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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