Synthesis of chiral cyclic α-p-tolylsulphinyl ketones
- 1 January 1989
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 7,p. 1335-1337
- https://doi.org/10.1039/p19890001335
Abstract
Two new syntheses of optically pure cyclic β-oxo sulphoxides are described. Reactions of (–)menthyl toluene-p-sulphinate with cycloalkanones (CH2)nCO (n= 4, 5, and 6) and PriNMgBr yield mixtures of diastereoisomeric sulphoxides without epimerization at sulphur. With the cyclopentanone (n= 4) yields are poor owing to competitive autocondensation of the keeone. Reactions of cycloalkanone N-phenylimines with the sulphinate in the presence of lithium di-isopropylamide afford, after chromatographic purification, the same mixtures of diastereoisomeric β-oxo sulphoxides with no aldolic condensation product.Keywords
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