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Polymer-supported (-)-8-phenylmenthyl auxiliary as an effective solid-phase chiral inductor in the addition of nucleophiles to N-acyliminium ions

Author(s):

Oscar Forero-Doria, Leonard S. Santos, Fabiane M. Nachtigall and Nagula Shankaraiah  

Abstract:


A facile approach for the addition of nucleophiles to N-acyliminium ion has been developed through solid-supported (˗)-8-phenylmenthyl auxiliary as an effective chiral inductor. This method has yielded higher ee/de% in nucleophilic additions through the Si-face of the polymer-supported N-acyliminium ion. Furthermore, the scope of this protocol using these key intermediates for the synthesis of alkaloids such as (S)-coniine, (R)-pelletierine and (R,R)-myrtine was also explored. Additionally, the key intermediates associated with this reaction were monitored and characterized by MALDI–TOF-MS.

Keywords:

(˗)-8-Phenylmenthyl chiral auxiliary, solid-phase synthesis, asymmetric nucleophilic addition, alkaloids, MALDI-MS, on-line monitoring.

Affiliation:

Laboratory of Asymmetric Synthesis, Chemistry Institute of Natural Resources, Talca University, Talca, Laboratory of Asymmetric Synthesis, Chemistry Institute of Natural Resources, Talca University, Talca, Instituto de Innovación Basada en Ciencia, University of Talca, Talca, Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad



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