Department of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland.
Chem Soc Rev. 2010 Feb;39(2):845-83. doi: 10.1039/b909358n. Epub 2009 Dec 7.
This critical review, which is relevant to researchers in synthetic organic chemistry, focuses on asymmetric 1,3-dipolar cycloadditions with acrylamides. The use of chiral acrylamides as dipolarophiles leads to high levels of stereocontrol, due to conformational constraint in the acrylamides. Employment of chiral tertiary acrylamides containing nitrogen heterocycles is particularly effective in controlling the stereoselectivity. Following a general overview of 1,3-dipolar cycloadditions, the main body of the review focuses on asymmetric 1,3-dipolar cycloadditions of acrylamides with nitrile oxides, nitrones, diazoalkanes and azomethine ylides, with particular emphasis on the rationale for the observed stereocontrol (215 references).
这篇评论性文章主要讨论了与合成有机化学领域的研究人员相关的手性 1,3-偶极环加成反应，重点关注丙烯酰胺的不对称反应。由于丙烯酰胺的构象限制，手性丙烯酰胺作为偶极子可以实现高水平的立体控制。使用含有氮杂环的手性叔丙烯酰胺可以特别有效地控制立体选择性。在对 1,3-偶极环加成反应进行概述之后，本文的主要内容集中在手性丙烯酰胺与腈氧化物、氮氧化物、重氮烷烃和亚胺叶立德的不对称 1,3-偶极环加成反应上，特别强调了观察到的立体控制的原理（215 篇参考文献）。
