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.

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.…”

Investigation of the Reaction of Allyl(cyclopentadienyl)iron(II) Dicarbonyl with Iminium Salts: Synthesis of Ammonium Salts of Substituted Five-Membered-Ring Iron Complexes

“…Cycloaddition reactions between transition-metal 2-alkynyl and η 1 -allyl complexes and unsaturated electrophilic reagents have been studied in detail over the last 30 years . The pioneering works in this area have been done by the groups of Rosenblum, Wojcicki, and Welker. 1c,d The [3 + 2] cycloaddition reactions of η 1 -allyl complexes have been shown to yield transition-metal-substituted heterocyclic as well as carbocyclic five-membered rings which offer alternative approaches to prepare these ring systems, when the metal moiety is subsequently removed from the ring. − The reaction of the lithium enolate of the pseudooctahedral complex (η 5 -Cp)Fe(PPh 3 )(CO)COCH 3 with Eschenmoser's iminium salt and the reactions of complex 1 with N -tosylimines, which are activated by Lewis acids such as BF 3 ·OEt 2 , ZnCl 2 , MgBr 2 , SnCl 4 , and TiCl 4 , have been reported in the literature. , As a continuation of our research devoted to the reaction of nucleophiles with iminium salts, , especially in situ generation of iminium ions, herein we report a new and practical entry to a series of interesting nitrogen-containing heterocyclic compounds (Scheme ).

1 Reaction of Complex 1 with Eschenmoser Salt

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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.…”