tert-Butanesulfinamide

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tert-Butanesulfinamide
(R)-tert-butylsulfinamide
(S)-tert-butylsulfinamide
Ball-and-stick model of tert-butanesulfinamide
Names
Preferred IUPAC name
2-Methylpropane-2-sulfinamide
Identifiers
3D model (
JSmol
)
ECHA InfoCard
 100.108.188 Edit this at Wikidata
UNII
  • (R/S): InChI=1S/C4H11NOS/c1-4(2,3)7(5)6/h5H2,1-3H3
    Key: CESUXLKAADQNTB-UHFFFAOYSA-N
  • (R)-(+): InChI=1S/C4H11NOS/c1-4(2,3)7(5)6/h5H2,1-3H3/t7-/m1/s1
    Key: CESUXLKAADQNTB-SSDOTTSWSA-N
  • (S)-(-): InChI=1S/C4H11NOS/c1-4(2,3)7(5)6/h5H2,1-3H3/t7-/m0/s1
    Key: CESUXLKAADQNTB-ZETCQYMHSA-N
  • (R/S): O=S(N)C(C)(C)C
  • (R)-(+): O=[S@@](N)C(C)(C)C
  • (S)-(-): O=[S@](N)C(C)(C)C
Properties
(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).
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tert-Butanesulfinamide (also known as 2-methyl-2-propanesulfinamide or Ellman's sulfinamide) is an

asymmetric synthesis as chiral auxiliaries, often as chiral ammonia equivalents for the synthesis of amines.[1][2][3] tert-Butanesulfinamide and the associated synthetic methodology was introduced in 1997 by Jonathan A. Ellman et al.[4]

Enantiopure synthesis

Enantiopure tert-butanesulfinamide can be prepared by enantioselective oxidation of inexpensive di-tert-butyl disulfide to the

3,5-di-tert-butyl salicylaldehyde
.

Tert-butanesulfinamide synthesis
Tert-butanesulfinamide synthesis
tert-Butanesulfinamide synthesis

Enantioselective amine synthesis

Condensation with

ammonium salt
or amine (from aldehyde precursor) or the chiral secondary amine (ketone precursor).

Tert-butanesulfinamide chiral amine synthesis
Tert-butanesulfinamide chiral amine synthesis
tert-Butanesulfinamide chiral amine synthesis

Typical nucleophiles are

organolithium compounds, and enolates
.

Chiral

sulfinimines as intermediates for the asymmetric synthesis of amines have also been developed by Franklin A. Davis.[5]

Applications

tert-Butanesulfinamide has been used as an auxiliary in an asymmetric synthesis of cetirizine (more potent than the racemic mixture of the drug) starting from p-chlorobenzaldehyde and phenylmagnesium bromide.[6]

Asymmetric sulfinamide cetirizine synthesis
Asymmetric sulfinamide cetirizine synthesis
Asymmetric cetirizine synthesis

References

  1. S2CID 97201636
    .
  2. PMID 20420386
    .
  3. ^ Organic Syntheses, Vol. 82, p.157 (2005). Link
  4. doi:10.1021/ja972012z
    .
  5. PMID 11671597
    .
  6. doi:10.1016/S0040-4039(01)02294-8
    .
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