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

Tomoya Miura; Takayuki Nakamuro; Kentaro Hiraga; Masahiro Murakami

doi:10.1039/c4cc04786a

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

Chem Commun (Camb). 2014 Sep 18;50(72):10474-7. doi: 10.1039/c4cc04786a.

Authors

Tomoya Miura¹, Takayuki Nakamuro, Kentaro Hiraga, Masahiro Murakami

Affiliation

¹ Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan. tmiura@sbchem.kyoto-u.ac.jp murakami@sbchem.kyoto-u.ac.jp.

PMID: 25068433
DOI: 10.1039/c4cc04786a

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.