立体选择性地合成杂芳亚甲基取代的吡咯烷：完全有机催化的曼尼希氨化反应。

Stereoselective access to heteroarylmethylene-substituted pyrrolidines: fully organocatalytic Mannich-hydroamination reactions.

机构信息

Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen, CNRS UMR, 6 boulevard du Marechal Juin, 14050 Caen, France.

出版信息

Chem Commun (Camb). 2013 Feb 25;49(16):1651-3. doi: 10.1039/c2cc38954a.

DOI:10.1039/c2cc38954a

PMID:23340658

Abstract

A one-pot sequence of organocatalytic transformations delivers heteroarylmethylene-substituted pyrrolidines with high stereo- and enantioselectivity. A Mannich coupling of N-heteroarylalkyne aldehydes with aldimine and an original metal-free hydroamination of the resulting adducts are the key transformations of the process delivering highly functionalized molecules with high potential for synthetic applications.

摘要

一锅法的有机催化转化过程可以高立体选择性和对映选择性地得到杂芳亚甲基取代的吡咯烷。该过程的关键转化是 N-杂芳基炔醛与亚胺的曼尼希缩合反应，以及生成的加合物的新型无金属氢胺化反应，这两个反应可以得到具有高合成应用潜力的高度官能化分子。