ADDITIVE AND MEDIUM EFFECTS ON LEWIS ACID-PROMOTED CATIONIC PI-CYCLIZATIONS OF ALKENYLCYCLOPENTANE-1,3-DIONES AND ALKYNYLCYCLOPENTANE-1,3-DIONES

被引：61

作者：

BALOG, A ^{[1
]}

GEIB, SJ ^{[1
]}

CURRAN, DP ^{[1
]}

机构：

[1] UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 02期

关键词：

D O I：

10.1021/jo00107a012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The effects of nucleophilic additives, Lewis and Bronsted acids, and solvents on BF3.Et(2)O-promoted cationic pi-cyclizations of alkynyl- and alkenylcyclopentane-1,3-diones are reported. The rates and selectivities of alkynyl dione cyclizations were significantly effected by the addition of external nucleophiles or water, and the regioselectivity of cyclization was effected by the choice of reaction solvent. Cyclizations of alkenyl diones, which fail under standard non-nucleophilic conditions, were found to be successful in the presence of added nucleophiles or with Lewis acids other than BF3.Et(2)O. The usefulness of these cationic pi-cyclizations for producing bicyclic ring systems of various functionality was also explored.

引用

页码：345 / 352

页数：8

共 22 条

[1] RING-ENLARGING ANNULATIONS - A ONE-STEP CONVERSION OF CYCLIC SILYL ACYLOINS AND OMEGA-ALKYNYL ACETALS TO POLYCYCLIC ENEDIONES [J].