Synthesis of cis,cis,cis-tetrasubstituted cyclobutanes. Trapping of tetrahedral intermediates in intramolecular nucleophilic addition
The intramolecular [2 + 2] photocycloaddition of bismaleimides leads to cage diimides 2. Nucleophilic addition on these compounds (NaBH4, RLi, or MeONa) gives rise to various diazatetracyclic 4 and 11 or oxadiazapentacyclic 3 "bowl shaped" alcohols. X-ray analyses of 3c and 11a provide definite structural data concerning these two highly functionalized compounds.
Laurenti
D
Laboratoire de Synthese Organique, ESA au CNRS no. 6009, Faculte des Sciences de St Jerome, Marseille, France.
Santelli-Rouvier
C
Pepe
G
Santelli
M