Benzosultams: Synthesis and Applications

Abstract

Recent developments on the synthesis and applications of benzosultams are reviewed. INTRUDUCTIONOppolzer's camphorsultam (1) 1 and its antipode were introduced in 1984 2 and rank today among the most practical of chiral auxiliaries available for organic synthesis.The structurally more simple relatives, the benzosultams (2) (R = Me, t-Bu, etc.), also make up an important class of chiral auxiliaries (Figure 1).These sultams have many important applications as chiral auxiliaries in asymmetric versions of several reactions, including alkylations, 3 acylations, 3 aldol reactions, 3 Diels-Alder reactions, 4 and azidations.][8][9][10][11] Recently, such benzosultams have also received much attention as potent HIV-1 inhibitors. 1 2 In this article, recent developments on the synthesis and applications of benzosultams are reviewed.Figure FIVE-MEMBERED BENZOSULTAMS Oppolzer's Chiral 3-Monosubstituted Five-membered BenzosultamsChiral 3-monosubstituted five-membered benzosultams have been developed as alternatives to the well-known Oppolzer camphorsultam auxiliary.The benzosultams have simpler structures and also possess a benzene chromophore that makes their detection easier.4][15][16] There are also other approaches reported for the preparation of the N-sulfonylimines (4). 17-192 NH O 2