Stereocontrolled synthesis of azeto[2,1-b] quinazolines bearing three stereocenters via the intramolecular [2+2] cycloaddition between ketenimines and imines

被引：19

作者：

Alajarín, M

Vidal, A

Tovar, F

de Arellano, MCR

机构：

[1] Univ Murcia, Fac Quim, Dept Quim Organ, E-30100 Murcia, Spain

[2] Univ Valencia, Fac Farm, Dept Quim Organ, Valencia 46100, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 03期

关键词：

2+2] cycloadditions; ketenimines; imines;

D O I：

10.1016/j.tetasy.2003.11.025

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A highly stereoselective synthesis of azeto[2,1-b]quinazolines bearing three stereocenters (Cl, C2, and CS) has been achieved via intramolecular [2+2] cycloaddition between ketenimine and imine functions supported on an ortho-benzylic scaffold. An asymmetric center adjacent to the iminic nitrogen atom, the future C8 carbon of the bicyclic product, efficiently controls the absolute configuration of the two new stereogenic carbon atoms of the azetidine ring, Cl and C2. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：489 / 494

页数：6

共 20 条

[1] New stereoselective intramolecular [2+2] cycloadditions between ketenimines and imines on an ortho-benzylic scaffold:: 1,4-asymmetric induction [J].