RESUMO
Trimethylsilyl triflate promotes Ferrier-Petasis rearrangement of 4-(vinyloxy)-, 4-(propenyloxy)-, and 4-(isopropenyloxy)azetidin-2-ones to corresponding 4-(carbonylmethyl)azetidin-2-ones. The latter compounds may serve as attractive intermediates in the synthesis of carbapenem antibiotics. To illustrate the potential of this reaction, selected rearrangement products have been transformed into carbapenams.
Assuntos
Azetidinas/química , Carbapenêmicos/síntese química , Cefalosporinas/síntese química , Carbapenêmicos/química , Cefalosporinas/química , Conformação Molecular , EstereoisomerismoRESUMO
The title compound, [Ni(2)(C(5)H(5))(C(10)H(15))(C(12)H(8))] or [Ni(C(10)H(15)){Ni(C(5)H(5))(C(12)H(8))}], is a rare example (and the first obtained from nickelafluorenyllithium) of an analogue of nickelocene in which the central Ni atom is coordinated to one pentamethylcyclopentadienyl ring and one nickelafluorenyl ring. Both rings lie almost parallel to one another: the dihedral angle between the planes which include these rings is 4.4 (1) degrees . Slip parameter analysis indicates that the bonding mode of the central Ni atom to the nickelacyclic ring is between eta(3) and eta(5). Two-dimensional layers of molecules are formed by C-H...pi interactions.