Enantiomerically pure sulphinyl-4,5-dihydroisoxazoles. Part 1. Stereocontrolled synthesis of optically active β-ketols and γ-amino alcohols
- 1 January 1985
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2289-2292
- https://doi.org/10.1039/p19850002289
Abstract
exo-Metallation of racemic 3-methyl-4,5-dihydroisoxazoles and reaction of the products with (–)-(S)-menthyl toluene-p-sulphinate afforded diastereoisomeric 3-sulphinylmethyl derivatives which can be separated and individually converted either into the corresponding enantio- and diastereoiso-merically pure 4,5-dihydroisoxazoles or β-ketols, depending on the desulphurization conditions; furthermore, stereoselective reduction of the former provides an entry to optically active γ-amino alcohols.Keywords
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