X=Y-ZH COMPOUNDS AS POTENTIAL 1,3-DIPOLES .44. ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION REACTIONS OF IMINES AND CHIRAL CYCLIC DIPOLAROPHILES

被引：71

作者：

COOPER, DM

GRIGG, R

HARGREAVES, S

KENNEWELL, P

REDPATH, J

机构：

[1] UNIV LEEDS,SCH CHEM,LEEDS LS2 9JT,W YORKSHIRE,ENGLAND

[2] ROUSSEL SCI INST,SWINDON SN3 5BZ,WILTS,ENGLAND

[3] ORGANON RES LABS LTD,NEWHOUSE ML1 5SH,LANARK,SCOTLAND

来源：

TETRAHEDRON | 1995年 / 51卷 / 28期

关键词：

D O I：

10.1016/0040-4020(95)00397-Q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Metallo - 1,3-dipoles generated in situ from both aryl and aliphatic imines of a-amino esters by the action of silver salts and tertiary amines undergo cycloaddition at room temperature to 5R-(1'R, 2'S, 5'R-menthyloxyl) - 2(5H)-furanone and to N-acetyl-5R-isopropoxy-2(5H)-pyrrolone giving homochiral cycloadducts in good yield in all cases. pi-Interaction between the dipolarophile carbonyl group and the aryl group in the aryl imines is not required for good induction. The stronger the base the faster the cycloaddition with 2-t-butyl-1,1,3,3-tetramethylguanidine > DBU > NEt(3). X-Ray crystal structures of representative cycloadducts establish the absolute configuration of the pyrrolidine stereocentres.

引用

页码：7791 / 7808

页数：18

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