89598-00-5

Upstream product

• 3518-65-8 monochloromethanesulfonyl chloride 
• 63126-47-6 (2S)-2-(methoxymethyl)-1-pyrrolidine 

Downstream Products

• 89598-47-0 (S)-1-(2-Benzyl-4,5-dimethyl-1-oxo-1,2,3,6-tetrahydro-1λ⁴-thiopyran-2-sulfonyl)-2-benzyloxymethyl-pyrrolidine 
• 89598-32-3 (S)-2-Benzyloxymethyl-1-(2-phenyl-1-trimethylsilanyl-ethanesulfonyl)-pyrrolidine 

Relevant academic research and scientific papers

Asymmetric synthesis of α,β-epoxy sulphonamides (oxiranesulphonamides)

The asymmetric phase-transfer-catalused (PTC) Darzens condensation of aldehydes and ketones with chiral reagents (S)-(-)-N-(chlormethylsulphonyl)-2-(methoxymethyl)pyrrolidine (2), (S)-(-)-tert-butyl N-(chlormethylsulphonylprolinate (4) and (+)-O-methyl-N-chlormethylsulphonyl)ephedrine (6), using triethylbenzylammonium chloride (TEBA) as the phase-transfer catalyst, to give optically active diastereomeric α,β-epoxy sulphonamides (oxiranesulphonamides), is described.Of the chiral reagents used, 2 was found to be the most effective, imparting an asymmetric induction of up to almost 50percent, as assessed by Eu(fod)3-resolved 1H NMR spectra.The stereochemical course of the asymmetric synthesis is discussed.

Asymmetric Diels-Alder Reactions with Sulfines Derived from Proline

The Synthesis of a variety of sulfines 8 derived from S-proline, utilizing the reaction of α-silyl carbanions with sulfur dioxide, is described.Reaction of the thus prepared sulfines 8 with 2,3-dimethyl-1,3-butadiene gave dihydrothiopyran S-oxides 9.During these cycloaddition reactions asymmetric inductions up to 40percent were observed.From one pure diastereomeric form of cycloadduct 9d an X-ray analysis was carried out in order to provide insight in the steric course of the cycloaddition reaction.