(+/-)-tert-butylsulfinamide
'''tert-Butanesulfinamide (also known as 2-methyl-2-propanesulfinamide or Ellman's sulfinamide') is an organosulfur compound and a member of the class of sulfinamides. Both enantiomeric forms are commercially available and are used in asymmetric synthesis as chiral auxiliaries, often as chiral ammonia equivalents for the synthesis of amines. tert-Butanesulfinamide and the associated synthetic methodology was introduced in 1997 by Jonathan A. Ellman et al''.
Article
4 sectionsContents
- Enantiopure synthesis
- Enantioselective amine synthesis
- Applications
- References
'''tert-Butanesulfinamide (also known as 2-methyl-2-propanesulfinamide or Ellman's sulfinamide') is an organosulfur compound and a member of the class of sulfinamides. Both enantiomeric forms are commercially available and are used in asymmetric synthesis as chiral auxiliaries, often as chiral ammonia equivalents for the synthesis of amines. tert-Butanesulfinamide and the associated synthetic methodology was introduced in 1997 by Jonathan A. Ellman et al.
==Enantiopure synthesis== Enantiopure tert-butanesulfinamide can be prepared by enantioselective oxidation of inexpensive di-tert-butyl disulfide to the thiosulfinate followed by disulfide bond cleavage by lithium amide. In the original scope the chiral ligand used together with vanadyl acetylacetonate was prepared by condensing an optically pure chiral aminoindanol with 3,5-di-tert-butyl salicylaldehyde.