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

Polymer-supported (-)-8-phenylmenthyl auxiliary as an effective solid-phase chiral inductor in the addition of nucleophiles to N-acyliminium ions.
Comb Chem High Throughput Screen. 2017 Jun 01;:
Authors: Forero-Doria O, Santos LS, Nachtigall FM, Shankaraiah N
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.
PMID: 28571539 [PubMed - as supplied by publisher]

Source: Combinatorial Chemistry and High Throughput Screening - June 1, 2017 Category: Chemistry Authors: Forero-Doria O, Santos LS, Nachtigall FM, Shankaraiah N Tags: Comb Chem High Throughput Screen Source Type: research