Sterically constrained 'roofed' 2-thiazolidinones as excellent chiral auxiliaries.
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.
Hoshimoto
S
S
Faculty of Pharmaceutical Sciences, Kumamoto University, Japan.
Matsunaga
H
H
Kunieda
T
T
D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism; D013844:Thiazoles / Q000737:chemistry*
D013844:Thiazoles