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Sterically constrained 'roofed' 2-thiazolidinones as excellent chiral auxiliaries
S Hoshimoto1, H Matsunaga, T Kunieda
1Faculty of Pharmaceutical Sciences, Kumamoto University, Japan.
Chemical & Pharmaceutical Bulletin
|October 25, 2000
Abstract:
The "roofed" chiral 2-thiazolidinones, which are sterically congested and conformational rigid, and which are prepared by the [4+2] cycloaddition of 2-thiazolone to the cyclic dienes, dimethylanthracene and hexamethylcyclopentadiene, followed by optical resolution with (1S,2R)-2-methoxy-1-apocamphanecarbonic acid (MAC acid) are of considerable promise for use as chiral auxiliaries for the alkylation of enolates.