Tetrahedron

Rotational features of carbon-nitrogen bonds in N-Aryl maleimides. Atroposelective reactions of o-tert-Butylphenylmaleimides

DP Curran, S Geib, N DeMello

Index: Curran, Dennis P.; Geib, Steven; DeMello, Nicholas Tetrahedron, 1999 , vol. 55, # 18 p. 5681 - 5704

Full Text: HTML

Citation Number: 76

Abstract

Atroposelective addition and cycloaddition reactions of N-2-(tert-butylphenyl)-and N-2, 5-(di- tert-butylphenyl) maleimide and a substituted derivative have been studied. Good to excellent stereoselectivities are generally observed, and high rotation barriers (about 29 kcal/mol) prevent the products from interconverting. Crystal structures of the precursors and products support a straightforward model where reactants attack trans to the o-tert-butyl ...