NEIGHBORING GROUP PARTICIPATION IN LEWIS ACID-PROMOTED [3+4] AND [3+5] ANNULATIONS - THE SYNTHESIS OF OXABICYCLO[3.N.1]ALKAN-3-ONES

被引：198

作者：

MOLANDER, GA

CAMERON, KO

机构：

[1] Department of Chemistry and Biochemistry, University of Colorado, Boulder

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1993年 / 115卷 / 03期

关键词：

D O I：

10.1021/ja00056a002

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Lewis acids are employed as catalysts in the annulation of 1,4- and 1,5-dicarbonyl dielectrophiles with bis(trimethylsilyl) enol ethers of beta-diketones and beta-keto esters. A variety of 2-(alkoxycarbonyl)-m-oxabicyclo[3.n.1]alkan-3-ones can be constructed by this process in which two new carbon-carbon bonds are generated Unusually high regiocontrol is observed, and good to excellent stereochemical control can be achieved at virtually every position on the new carbocycles. Intramolecular neighboring group participation is proposed to explain the unusually high selectivities attained in the annulation reaction.

引用

页码：830 / 846

页数：17

共 109 条

[41] NUCLEOPHILIC ORGANO-SILICON INTERMEDIATES TURNED ELECTROPHILIC - (TRIMETHYLSILYL)METHYL, TRIMETHYLSILYLOXY AND ALSO 2-TETRAHYDROPYRANYLOXY AS TERMINATORS OF CYCLO-ADDITIONS OF ALLYL CATIONS - A SHORT ROUTE TO DEHYDROZIZAENES (6-METHYLENETRICYCLO[6.2.1.01,5]-UNDEC-9,10-ENES) AND RELATED TRICYCLES AND [3.2.1]-BICYCLESI [J].