Spiro-cyclopropanation from oxoallylsilanes.
A novel highly stereoselective spiro-cyclopropanation reaction from oxoallylsilanes is described. Oxoallylsilanes are readily obtained by silylcupration of allene followed by conjugate addition to enones. The former oxoallylsilanes undergo a tandem cyclization-cyclopropanation reaction when treated with CH2I2/Me3Al, leading to hydroxylated polycyclic systems bearing the spiro-cyclopropane moiety. The scope of the process is studied, and a feasible pathway is discussed.
Barbero
Asunción
A
Departamento de Química Orgánica, Universidad de Valladolid, 47011 Valladolid, Spain.
Castreño
Pilar
P
Pulido
Francisco J
FJ
D001685:Biological Factors / Q000138:chemical synthesis; D003500:Cyclization; D003521:Cyclopropanes / Q000138:chemical synthesis*; D012821:Silanes / Q000138:chemical synthesis / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis*
D001685:Biological Factors; D003521:Cyclopropanes; D012821:Silanes; D013141:Spiro Compounds