The LiClO4-Mediated Synthesis of β-(Dialkylamino) Sulfoxides and β-(Dialkylamino) Sulfones by Addition of α-Lithiated Salts of Sulfoxides and Sulfones to Aldehydes and (Trimethylsilyl)dialkylamines

Abstract

The LiClO4‐mediated one‐pot reaction of aldehydes with (trimethylsilyl)dialkyl amines and the lithium salt of sulfoxides or sulfones, affords the corresponding β‐(dialkylamino) sulfoxides and β‐(dialkylamino) sulfones in high yields. The aminosulfoxidation reaction of aliphatic or aromatic aldehydes lacks diastereoselectivity, but the diastereomeric sulfoxides can be separated by HPLC or column chromatography for further use.

Synthesis, and antimicrobial activity of 2,10-dichloro–6- substituted aminobenzyl–12H –dibenzo [d, g][1,3,2]dioxaphosphocin– 6–oxides

“…Hydrolysis of 3 gave the corresponding cyclic hydrogen phosphite (4) 11 . The reaction of both phosphorobromodite (3)/ cyclic hydrogenphosphite (4) with various aldehydes and amines in dry toluene at 50-60°C afforded the title compounds in good yields.…”

Multicomponent Mannich‐Like Reactions of Organometallic Species

“…The same concept of using stabilized lithiated species was further exploited by Saidi and co‐workers in the case of α‐lithiated salts of sulfoxides and sulfones 60 . In this case, the aminoalkylation reaction led to new functionalized β‐(dialkylamino) sulfoxides and sulfones 61 (Scheme ).…”

Organosilicon Compounds as Water Scavengers in Reactions of Carbonyl Compounds

“…50,[55][56][57] First, it was shown that aromatic and heteroaromatic aldehydes were aminoalkylated by trimethylsilylamines in the presence of lithium perchlorate. [58][59][60][61][62][63] Imines or iminium salts formed in the first step of the reaction were trapped by the corresponding nucleophile to afford corresponding amines 69, 70 (Scheme 41). Later, the approach was modified in order to allow trimethylsilylamines to be generated in situ.…”