Issue 24, 1999

Studies towards the preparation of sparteine-like diamines for asymmetric synthesis

Abstract

A route for the preparation of sparteine-like diamines starting from naturally occurring amino acids has been explored. Starting from the amino acids (S )-proline and (S )-phenylalanine, two novel sparteine-like diamines 2 and 3 have been prepared. The synthetic route involves Dieckmann condensation followed by a double Mannich reaction to set up the tricyclic structure with control of the relative stereochemistry. During the Dieckmann and Mannich reactions it was found that racemisation occurred either via retro-Michael or retro-Mannich processes. Conditions for preventing racemisation in the Dieckmann reaction were uncovered but it was not possible to prevent racemisation during the double Mannich reaction. Thus, the two novel sparteine-like diamines 2 and 3 have been prepared in racemic form.

Supplementary files

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1999, 3623-3631

Studies towards the preparation of sparteine-like diamines for asymmetric synthesis

J. R. Harrison, P. O’Brien, D. W. Porter and N. M. Smith, J. Chem. Soc., Perkin Trans. 1, 1999, 3623 DOI: 10.1039/A906969K

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