α-亚氨基酯的催化不对称炔基化反应：一种合成光学活性非天然α-氨基酸衍生物的通用方法。
Catalytic asymmetric alkynylation of alpha-imino ester: a versatile approach to optically active unnatural alpha-amino acid derivatives.
作者信息
Ji Jian-Xin, Wu Jing, Chan Albert S C
机构信息
Open Laboratory of Chirotechnology, Institute of Molecular Technology for Drug Discovery and Synthesis, and Department of Applied Biology and Chemical Technology, Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong.
出版信息
Proc Natl Acad Sci U S A. 2005 Aug 9;102(32):11196-200. doi: 10.1073/pnas.0502105102. Epub 2005 Aug 1.
Abstract
The catalytic asymmetric introduction of alkynyl functionality to alpha-amino acid derivatives was realized by the direct addition of terminal alkynes to alpha-imino ester in the presence of chiral Cu(I) complex under mild reaction conditions. Owing to the rich chemistry to which alkyne can be subjected, the present system provides a remarkably versatile tool for the construction of optically active alpha-amino acid derivatives. Good yields and enantiomeric excess values were achieved with an array of terminal alkynes and challenging, biologically active, unnatural alpha-amino acid derivatives could be conveniently obtained.
摘要
在手性铜（I）配合物存在下，通过在温和反应条件下将末端炔烃直接加成到α-亚氨基酯上，实现了向α-氨基酸衍生物中催化不对称引入炔基官能团。由于炔烃可参与丰富的化学反应，本体系为构建光学活性α-氨基酸衍生物提供了一种非常通用的工具。使用一系列末端炔烃可实现良好的产率和对映体过量值，并且可以方便地获得具有挑战性的、生物活性的非天然α-氨基酸衍生物。
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