94992-27-5

Upstream product

• 89818-50-8 (+)-(R)-1-Phenyl ethyl 2-pyridyl sulfide 
• 89818-49-5 (S-)-(-) 1-phenylethyl 2-pyridyl sulfide 

Downstream Products

• 89818-51-9 (+)-(S)-2-(1-methylbenzyl)pyridine 
• 89818-52-0 (R)-(-)-2-(1-phenylethyl)pyridine 
• 112498-17-6 1-Methyl-2-((R)-1-phenyl-ethyl)-pyridinium; iodide 

Relevant academic research and scientific papers

LIGAND COUPLING THROUGH ?-SULFURANE --- COMPLETE RETENTION OF CONFIGURATION OF 1-PHENYLETHYL GROUP IN THE REACTION OF 1-PHENYLETHYL 2-PYRIDYL SULFOXIDE WITH GRIGNARD REAGENT

The reaction of benzyl or 1-phenylethyl 2-pyridyl sulfoxide with Grignard reagent proceeds via a ?-sulfurane as an intermediate to give the coupling product, 2-benzylpyridine or 2-(1-phenylethyl)pyridine in quantitative yield.Stereochemistry for this reaction is complete retention at the benzylic carbon atom.

Ligand Coupling within ?-Sulphurane Intermediates formed in the Reaction of Benzyl 2-Pyridyl and Related Sulphoxides with Grignard reagents

The reaction of benzyl or 1-phenylethyl 2-pyridyl sulphoxide (1) or (18) with a Grignard reagent was found to give the ligand-coupling product, i.e., 2-benzylpyridine or 2-(1-phenylethyl)pyridine (2) or (22) in excellent yield.This coupling reaction was found to proceed whithin the ?-sulphurane formed as an intermediate upon treatment of benzyl 2-pyridyl and related sulphoxides with a Grignard reagent.The stereochemical course of this coupling reaction involves complete retention at the benzylic carbon.