Camphorsultam, or Oppolzer's sultam, is a classic chiral auxiliary.
In the total synthesis of manzacidin B, Ohfune group utilized camphorsultam to construct the core oxazoline ring asymmetrically. Comparing with oxazolidinone as the chiral auxiliary, camphorsultam had a significant (2S,3R)-selectivity.
Camphorsultam also acts as a chiral auxiliary in Michael addition. Lithium base promoted stereoselective Michael addition of thiols to N-mcthacryloylcamphorsultam produced the corresponding addition products in high diastereoselectivity.
Camphorsultam was used as a chiral auxiliary for the asymmetric Claisen rearrangement. In the presence of butylated hydroxytoluene (BHT) used as a radical scavenger, a toluene solution of the adduct between geraniol and camphorsultam was heated in a sealed tube at 140 °C, to provide mainly the (2R,3S)-isomer as the major rearrangement product in 72% yield, securing the two contiguous stereocenters including the quaternary carbon.