Lewis 碱催化下非稳定亚胺叶立德的 1,3-偶极环加成反应。

1,3-Dipolar cycloaddition of unstabilised azomethine ylides by Lewis base catalysis.

机构信息

Monash University, Clayton 3800, Melbourne, Australia.

出版信息

Org Biomol Chem. 2012 Oct 21;10(39):7903-11. doi: 10.1039/c2ob26047f.

Abstract

Lewis base catalysed 1,3-dipolar cycloaddition between α,β-unsaturated acyl fluorides and N-[(trimethylsilyl)methyl]amino ethers has been achieved using 1 mol% DMAP. Competition experiments and (19)F-NMR studies indicate that the cycloaddition occurs preferentially between the α,β-unsaturated acyl fluoride and the unstabilised azomethine ylide. In addition, an enantioselective variant, using chiral isothiourea catalysts, has been achieved with 14% ee.

摘要

Lewis 碱催化的α,β-不饱和酰氟与 N-[(三甲基硅基)甲基]甲氨基醚的 1,3-偶极环加成反应，使用 1 mol% DMAP 即可实现。竞争实验和（19）F-NMR 研究表明，环加成反应优先发生在α,β-不饱和酰氟和未稳定的亚胺叶立德之间。此外，使用手性异硫脲催化剂还实现了对映选择性变体，对映体过量值为 14%。