Tert-Butanesulfinamide

tert-Butanesulfinamide

Names
IUPAC name 2-Methyl-2-propanesulfinamide
Identifiers
CAS Number	146374-27-8 Y
3D model (JSmol)	Interactive image
ChemSpider	2627606 Y
ECHA InfoCard	100.108.188
PubChem CID	3382465
InChI InChI=1S/C4H11NOS/c1-4(2,3)7(5)6/h5H2,1-3H3 Y Key: CESUXLKAADQNTB-UHFFFAOYSA-N Y InChI=1/C4H11NOS/c1-4(2,3)7(5)6/h5H2,1-3H3 Key: CESUXLKAADQNTB-UHFFFAOYAH
SMILES O=S(N)C(C)(C)C
Properties
Chemical formula	(CH3)3CS(O)NH2
Molar mass	121.20 g/mol
Appearance	white to off-white crystalline solid
Melting point	102 to 105 °C (216 to 221 °F; 375 to 378 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is Y ?)
Infobox references

tert-Butanesulfinamide is an organosulfur compound and a member of the class of sulfinamides. Both enantiomeric forms are commercially available and are relevant to the asymmetric synthesis of amines as a chiral ammonia equivalent. This methodology was introduced in 1997 by Jonathan A. Ellman.

Chiral 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 a chiral aminoindanol with 3,5-di-tert-butyl salicylaldehyde.

Condensation with ketones and aldehydes yield the corresponding N-tert-butanesulfinyl aldimines and ketimines. These intermediates are more resistant to hydrolysis than other imines but more reactive towards nucleophiles. A nucleophile adds diastereoselectively over the imine group in an electrophilic addition with the tert-butanesulfinyl group acting as a chiral auxiliary. This tert-butanesulfinyl group is also a protecting group. On addition of hydrochloric acid the tert-butanesulfinyl group is removed forming the chiral primary ammonium salt or amine (from aldehyde precursor) or the chiral secondary amine (ketone precursor).