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

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.

DOI: 10.2174/1386207320666170602085724

Cite this paper

@article{ForeroDoria2017PolymersupportedA, title={Polymer-supported (-)-8-phenylmenthyl auxiliary as an effective solid-phase chiral inductor in the addition of nucleophiles to N-acyliminium ions.}, author={Oscar Forero-Doria and L S Santos and Fabiane M. Nachtigall and Nagula Shankaraiah}, journal={Combinatorial chemistry & high throughput screening}, year={2017} }