Diastereoselective intramolecular Diels-Alder reaction of the furan diene, a facile access to enantiopure epoxy tetrahydroisoindolines.

被引：29

作者：

Andres, C

Maestro, G

Nieto, J

Pedrosa, R

GarciaGranda, S

PerezCarreno, E

机构：

[1] UNIV VALLADOLID,FAC CIENCIAS,DEPT QUIM ORGAN,E-47011 VALLADOLID,SPAIN

[2] UNIV OVIEDO,FAC QUIM,DEPT QUIM FIS & ANALIT,E-33006 OVIEDO,SPAIN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 08期

关键词：

D O I：

10.1016/S0040-4039(97)00058-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-(2'-Furfuryl)-N-acryloyl tehahydro-1,3-benzoxazine 2a participates in diastereoselective intramolecular Diels-Alder reaction in very mild conditions leading to two diastereoisomeric exo-adducts with good diastereoselectivity. Chromatographic separation of both adduts, and further elimination of the menthol appendage allows to prepare enantiopure iso-indoline derivatives in excellent chemical yields. (C) 1997 Elsevier Science Ltd.

引用

页码：1463 / 1466

页数：4

共 19 条

[1] Synthesis of enantiopure primary amines by stereoselective ring opening of chiral octahydro-1,3-benzoxazines by grignard and organoaluminum reagents [J].