2014
DOI: 10.1021/jo500174a
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1-(N-Acylamino)alkyl Sulfones from N-Acyl-α-amino Acids or N-Alkylamides

Abstract: A variety of N-(1-methoxyalkyl)amides or carbamates react readily with sodium aryl sulfinates in the presence of triphenylphosphonium tetrafluoroborate or bromide in CHCl3 under mild conditions to give 1-(N-acylamino)alkyl sulfones in good yields. A combination of this reaction with the recently described electrochemical decarboxylative α-methoxylation of N-acyl-α-amino acids to give N-(1-methoxyalkyl)amides in the presence of 3-(1-piperidino)propyl-functionalized silica gel (SiO2-Pip) enables an effective two… Show more

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Cited by 29 publications
(12 citation statements)
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“…126 These α -amidoalkylating agents can in turn be converted into amidosulfones which are commonly used surrogates for acyl iminiums. 127 N -[1-(Benzotriazol-1-yl)alkyl]amides may be obtained in a similar fashion. 128 …”
Section: Anodic Oxidationmentioning
confidence: 99%
“…126 These α -amidoalkylating agents can in turn be converted into amidosulfones which are commonly used surrogates for acyl iminiums. 127 N -[1-(Benzotriazol-1-yl)alkyl]amides may be obtained in a similar fashion. 128 …”
Section: Anodic Oxidationmentioning
confidence: 99%
“…Applications of 1-( N -acylamino)alkyltriphenylphosphonium salts 4 (Ar = Ph) in the α-amidoalkylation of heteronucleophiles have been reported many times in the literature [5,6,7,8,10]. Usually in these types of reactions, it was necessary to use base catalysts, elevated temperature, and microwave irradiation.…”
Section: Resultsmentioning
confidence: 99%
“…N-[1-(p-Toluenesulfonyl)ethyl]pivalamide ( 10c ) [5]. Colorless crystals (124.7 mg, 88% yield), mp 143–145 °C.…”
Section: Methodsmentioning
confidence: 99%
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