Tetrahedron

Spirobicyclic diamines. Part 3: Synthesis and metal complexation of proline-derived [4.4]-spirodiamines

F Kelleher, S Kelly, V McKee

Index: Kelleher, Fintan; Kelly, Sinead; McKee, Vickie Tetrahedron, 2007 , vol. 63, # 37 p. 9235 - 9242

Full Text: HTML

Citation Number: 11

Abstract

The syntheses of racemic and homochiral [4.4]-spirolactams, starting from l-proline, in good yields are described. Reduction of the lactam carbonyl group of spirolactams, containing chiral substituents on the lactam nitrogen, with lithium aluminium hydride, gives a series of homochiral [4.4]-spirodiamines. The crystal structure of one of these spirodiamines on complexation with zinc chloride was obtained. Interestingly it showed a hydrogen-bonded ...