Synthesis of enantiomerically pure 2,5-disubstituted tetrahydrofurans using readily prepared (2S)-1-phenylsulphonylalkan-2-ols
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 1799-1803
- https://doi.org/10.1039/p19870001799
Abstract
Enantiomerically pure (2S)-1-phenylsulphonylalkan-2-ols [S—(1)] have been prepared from 1-chloro3-phenylsulphonylpropan-2-one (2) by the following successive procedures: reduction with baker's yeast, epoxidation with silver(I) oxide, and alkylation with a Grignard reagent. Alkylation of dianions of S—(1), followed by phenylselenocyclization gave enantiomerically pure 2,5-disubstituted tetrahydrofurans [S-(8)] with high regioselectivity.This publication has 6 references indexed in Scilit:
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