Stereoselective Quaternization of α-Amino Phenylacetonitriles Mediated by a Remote Sulfinyl Group
| Autor: | Inés Alonso, Francisco Tato, Ana M. Martín-Castro, José L. García Ruano |
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| Rok vydání: | 2007 |
| Předmět: |
Anions
Models Molecular Alkylating Agents Acetonitriles Magnetic Resonance Spectroscopy Stereochemistry Imine Chemistry Organic Molecular Conformation Stereoisomerism Lithium Chemical synthesis Acylation chemistry.chemical_compound Hydrocyanation Chemistry Organic Chemistry Benzene Sulfoxide Carbon Oxygen Models Chemical Electrophile Stereoselectivity Protons Sulfur |
| Zdroj: | The Journal of Organic Chemistry. 72:5994-6005 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo0705519 |
| Popis: | Enantiomerically pure alpha-substituted alpha-amino phenylacetonitriles have been readily prepared from 2-p-tolylsulfinylbenzaldimines following a two-step sequence: a moderately stereoselective hydrocyanation of the imines and a completely stereoselective quaternization of the resulting diastereoisomeric mixture of alpha-amino phenylacetonitriles with different alkylating or acylating reagents in the presence of KHMDS. Theoretical calculations support a stereoselectivity control exerted by the remote sulfinyl group, as long as it is responsible for the conformational preferences of the benzyllithium intermediates, which suffer the attack of the electrophiles to the less hindered diastereotopic face. |
| Databáze: | OpenAIRE |
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