Sulfamidation of 2-Arylaldehydes and Ketones with Chloramine-T

A series of aliphatic and aromatic carbonyl compounds has been transformed into the corresponding sulfamidated products by means of amine-catalyzed nitrene transfer of chloramine-T. Depending on the residues R, either α-sulfamidation in the case of aromatic aldehydes and acetone derivatives or direc...

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Bibliographic Details
Published inOrganic letters Vol. 8; no. 17; pp. 3797 - 3800
Main Authors Baumann, Thomas, Bächle, Michael, Bräse, Stefan
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.08.2006
Amer Chemical Soc
Subjects
Aldehydes - chemical synthesis
Amination
Amino Acids - chemical synthesis
Amino Acids - chemistry
Catalysis
Chemistry
Chemistry, Organic
Chloramines - chemistry
Ketones - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
Sulfur Compounds - chemistry
Tosyl Compounds - chemistry
CHIRAL NITRIDOMANGANESE COMPLEX
ENANTIOSELECTIVE AZIRIDINATION
COPPER-COMPLEXES
ASYMMETRIC HETEROGENEOUS AZIRIDINATION
ATOM-TRANSFER
ALKENE AZIRIDINATION
OLEFINS
SALEN-TYPE-LIGANDS
CARBOXYLIC-ACIDS
STYRENE DERIVATIVES
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Summary:A series of aliphatic and aromatic carbonyl compounds has been transformed into the corresponding sulfamidated products by means of amine-catalyzed nitrene transfer of chloramine-T. Depending on the residues R, either α-sulfamidation in the case of aromatic aldehydes and acetone derivatives or direct sulfamidation at the carbonyl functionality of aliphatic aldehydes has been observed. Applying microwave conditions, good to excellent yields under significantly reduced reaction times could be obtained, thus providing a facile access to α,α-disubstituted amino acids.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol061410g