2-SUBSTITUTED (E)-2-(2-LITHIOETHENYL)-1,3-DIOXOLANES - NEW DIASTEREOISOMERIC PURE BETA-ACYLVINYL ANION EQUIVALENTS

Authors
BACHKI A FOUBELO F YUS M
Citation
A. Bachki et al., 2-SUBSTITUTED (E)-2-(2-LITHIOETHENYL)-1,3-DIOXOLANES - NEW DIASTEREOISOMERIC PURE BETA-ACYLVINYL ANION EQUIVALENTS, Tetrahedron letters, 35(41), 1994, pp. 7643-7646
Citations number
57
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
41
Year of publication
1994
Pages
7643 - 7646
Database
ISI
SICI code
0040-4039(1994)35:41<7643:2(-ND>2.0.ZU;2-Q
Abstract
The reaction of (E)-chloroketals 1 with lithium powder and a catalytic amount of DTBB (4 mol %) in THF at -90 degrees C followed by treatmen t with different electrophiles [H2O, D2O, Bu(t)CHO, PhCHO, Me(2)CO,(CH 2)(4)CO, PhCOMe] at -90 to -60 degrees C affords, after hydrolysis wit h water, the expected functionalised protected (E)-alpha,beta-unsatura ted ketones 3. The deprotection of products 3 is easily achieved with silica gel/aqueous oxalic acid (cat.) to yield (E)-functionalised alke nones 5.