Instituto Universitario de Bio-Orgánica Antonio González, Departamento de Química Orgánica, Universidad de La Laguna, C/Astrofísico Francisco Sánchez 2, 38206 La Laguna, Tenerife, Spain.
Org Lett. 2010 Nov 19;12(22):5334-7. doi: 10.1021/ol102372c. Epub 2010 Oct 22.
An efficient alkene aza-Cope-Mannich cyclization between 2-hydroxy homoallyl tosylamine and aldehydes in the presence of iron(III) salts to obtain 3-alkyl-1-tosyl pyrrolidines in good yields is described. The process is based on the consecutive generation of a γ-unsaturated iminium ion, 2-azonia-[3,3]-sigmatropic rearrangement, and further intramolecular Mannich reaction. Iron(III) salts are also shown to be excellent catalysts for the new aza-Cope-Mannich cyclization using 2-hydroxy homopropargyl tosylamine.
在铁(III)盐存在下，2-羟基 homoallyl 对甲苯磺酰胺和醛之间发生有效的烯键氮杂-Cope-Mannich 环化反应，以高产率得到 3-烷基-1-对甲苯基吡咯烷。该过程基于γ-不饱和亚胺离子的连续生成、2-氮杂-[3,3]-sigma 重排以及进一步的分子内曼尼希反应。铁(III)盐也被证明是使用 2-羟基 homopropargyl 对甲苯磺酰胺的新型氮杂-Cope-Mannich 环化反应的优异催化剂。
