RESUMO

A highly regio- and stereoselective synthesis of novel ß,γ-disubstituted γ-lactams with either an anti or syn relative configuration was developed from readily available epoxide and aziridine acetates. The key steps include the regio- and diastereocontrolled nucleophilic ring-opening of these three-membered heterocycles followed by mild reductive cyclization of the γ-azido ester intermediate. The method was also extended to an asymmetric synthesis of (4R,5S)-4-hydroxy-5-phenylpyrrolidin-2-one from a chiral epoxide acetate. The main features of this versatile synthesis of functionalized γ-lactams include the involvement of inexpensive reagents and mild conditions together with high chemical efficiency.

Assuntos

Acetatos/química , Aziridinas/química , Compostos de Epóxi/química , Pirrolidinonas/química , Pirrolidinonas/síntese química , beta-Lactamas/química , beta-Lactamas/síntese química , Indicadores e Reagentes/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Estereoisomerismo

RESUMO

The mol-ecule of the title compound, C(18)H(16)N(2)O(4), adopts a T-shaped conformation with E stereochemistry for the imine double bond. The (3-nitro-benzyl-idene)amino fragment is almost planar, the mean planes of phenyl ring and nitro group forming a dihedral angle of 8.9 (3)°. In the 3-phenyl-acryloyl unit, the acrylic ester fragment is also almost planar, with the phenyl ring twisted by 41.44 (7)°. In the crystal, the mol-ecules are linked by C-H⋯O hydrogen-bond inter-actions into chains running parallel to [01].