Functionalized esters as bis-electrophiles in a silicon-induced domino synthesis of annulated carbocycles

…, G Harms, E Schaumann, M Gjikaj, G Adiwidjaja

Index: Genrich, Florian; Harms, Guido; Schaumann, Ernst; Gjikaj, Mimoza; Adiwidjaja, Gunadi Tetrahedron, 2009 , vol. 65, # 28 p. 5577 - 5587

Full Text: HTML

Citation Number: 6

Abstract

The reaction of silyl-substituted carbanion 1b with arene-1, 2-dicarboxylates 6, 15 yields indenone derivatives 11, 16 in a domino process involving silyl C→ O migration and elimination. However, in a competing pathway, the initial addition of 1b leads to lactone formation (8, 17). Substrates 26, 38 containing an ester group and a bromine substituent react with 1b under substitution of the halogen not allowing silyl migration. But desilylation ...