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

TETRAHEDRON

卷:63

Article

Kelleher, Fintan^1,2  Kelly, Sinead¹  Mckee, Vickie³ 

[1] Inst Technol Tallaght, Dept Sci & Adv Smart Mat Ctr, Dublin, Ireland

[2] Inst Technol Tallaght, Natl Inst Cellular Biotechnol, Dublin, Ireland

[3] Loughborough Univ, Dept Chem, Loughborough LE11 3TU, Leics, England

关键词: spirolactam;    spirodiamines;    synthesis;    x-ray crystal structure;    dimer;   

DOI  :  10.1016/j.tet.2007.06.050

来源: Elsevier

【 摘 要 】

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. (C) 2007 Elsevier Ltd. All rights reserved.

【 授权许可】

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