An exploratory study of type II [3 + 4] cycloadditions between vinylcarbenoids and dienes.
The intramolecular type II [3 + 4] cycloaddition between vinylcarbenoids and furans is a practical method for the construction of 5-oxo-10-oxatricyclo[6.2.1.0(4,9)]undeca-3, 8(11)-dienes, containing two anti-Bredt double bonds. These tricyclic systems are well functionalized for eventual elaboration to the natural product CP-263,114. The rhodium-stabilized vinylcarbenoids are generated by dirhodium tetracarboxylate catalyzed decomposition of vinyldiazoacetates. The [3 + 4] cycloaddition is generally considered to occur by a tandem cyclopropanation/Cope rearrangement, although evidence is presented that with these substrates the [3 + 4] cycloaddition may occur in a concerted manner.
Davies
H M
HM
Department of Chemistry, State University of New York at Buffalo, 14260-3000, USA.
Calvo
R L
RL
Townsend
R J
RJ
Ren
P
P
Churchill
R M
RM
D000475:Alkenes / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D005663:Furans / Q000737:chemistry*; D008299:Maleic Anhydrides / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D014753:Vinyl Compounds / Q000737:chemistry*
D000475:Alkenes; C104957:CP 263114; D004791:Enzyme Inhibitors; D005663:Furans; D008299:Maleic Anhydrides; D014753:Vinyl Compounds