Spirobicyclic Diamines. Part 3: Synthesis and Metal Complexation of Proline-Derived [4,4]-Spirodiamines.

Authors

Fintan Kelleher, Technological University DublinFollow
Sinead Kelly, Technological University Dublin
Vickie McKee, Loughborough University

Document Type

Article

Rights

Available under a Creative Commons Attribution Non-Commercial Share Alike 4.0 International Licence

Disciplines

Organic Chemistry

Publication Details

Tetrahedron, Vol. 63, Issue 37, 10 September, 2007, pp. 9235-9242

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 dimeric structure, where the monomers are diastereoisomeric diamines.

Recommended Citation

Kelleher, F., Kelly, S,. McKee, V., : Spirobicyclic Diamines. Part 3: Synthesis and Metal Complexation of Proline-Derived [4,4]-Spirodiamines. Tetrahedron, Vol. 63 (37) 10th Septemner, 2007, pp. 9235-9242, DOI : 10.1016/j.tet. 2007.06.050

Funder

Irish Government