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

作者:Miura Tomoya*; Nakamuro Takayuki; Hiraga Kentaro; Murakami Masahiro
来源:Chemical communications, 2014, 50(72): 10474-10477.
DOI:10.1039/c4cc04786a

摘要

A new procedure for the stereoselective synthesis of syn alpha-amino beta-oxy ketones is reported. It consists of two steps; in the first step, alpha-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 alpha-amino beta-oxy ketones with excellent syn-selectivity.

  • 出版日期2014