Enzymatic Approach to the Synthesis of Enantiomerically Pure Hydroxy Derivatives of 1,3,5-Triaza-7-phosphaadamantane

Abstract

A series of enantiomerically pure derivatives of 6-(1-hydroxyalkyl)-1,3,5-triaza-7-phosphatricyclo[3.3.1.1]decane 5 were successfully synthesized for the first time. A series of hydrolytic enzymes was applied in a stereoselective acetylation performed under kinetic resolution conditions. Although the secondary alcohols: α-aryl-hydroxymethyl-PTA (phosphines) 5b–d′ , PTA-oxides 8b–d′ , and PTA-sulfides 9b–d′ were found to be totally unreactive in the presence of all the enzymes and various conditions applied, the primary alcohols, i.e., the hydroxymethyl derivatives PTA oxide 8a and PTA sulfide 9a , were successfully resolved into enantiomers with moderate to good enantioselectivity (up to 95%). The absolute configurations of the products were determined by an X-ray analysis and chemical correlation.

The Backbone of Success of P,N-Hybrid Ligands: Some Recent Developments

“…P,N-chelation could be demonstrated by coordination to a W(CO) 4 fragment. Kwiatkowska and co-workers [88] recently reported the first examples of enantiomerically pure PTA ligands using a series of hydrolytic enzymes in a stereoselective acetylation performed under kinetic resolution conditions.…”