Tetrahedron letters

1-Vinyl-4-methyl-2, 6, 7-trioxabicyclo [2.2. 2] octanes: Unsaturated homoenolate anion equivalents

SK Richardson, A Jeganathan, DS Watt

Index: Richardson, Stewart K.; Jeganathan, Alwarsamy; Watt, David S. Tetrahedron Letters, 1987 , vol. 28, # 21 p. 2335 - 2338

Full Text: HTML

Citation Number: 19

Abstract

Abstract The metalation of (E)-1-(2-chlorovinyl)-or (E)-1-(2-bromovinyl)-4-methyl-2, 6, 7- trioxabicyclo [2.2. 2] octane with tert-butyllithium produced an unsaturated homoenolate anion equivalent which intercepted alkyl halides, aldehydes, ketones, and lactones to afford β-alkylated or β-acylated orthoesters, which, in turn, furnished β-substituted acrylate esters.