Document Type

Article

Rights

This item is available under a Creative Commons License for non-commercial use only

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.

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