Either enantiomer of tert-butanesulfinamide can be reached from tert-butyl disulfide in two steps: a catalytic asymmetric oxidation reaction gives the disulfide oxidation product (thiosulfinate) in high yield and enantiomeric excess. Treatment of this compound with lithium amide in ammonia affords optically pure inverted product.
<br />
Condensation of tert-butanesulfinamide with an aldehyde or ketone proceeds in high yield and affords only the (E)-isomer of the corresponding N-sulfinyl imines.
<br />