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- W2014429863 abstract "Enantiopure (S) benzyl and t-butyl 2-p-tolysulfinylpropenoates (1 and 2) were readily prepared by Mannich condensation of (R p-tolysulfinylacetates (Ch2O+Me2NH), followed by in situ nitrogen quaternization. These new chiral dienophiles reacted with furan at high pressures (4–13 Kbar) at rt to afford maily a 2:1 mixture of both endo adducts (itendo-B+endo-A). Enantiopure endo-4B and endo-4A were stereoselectively transformed into (+)-shikimic acid and (+)-5-epi-shikimic acid respectively, by dihydroxylation of the double bond, removal of the sulfinyl group, basic opening of the oxabicyclic skeleton and hydrolysis of the ester moiety." @default.
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- W2014429863 date "1997-05-01" @default.
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- W2014429863 title "Enantioselective synthesis of (+)-shikimic acid and (+)-5-epi-shikimic acid by asymmetric Diels-Alder reaction of (S)-α-sulfinylacrylates" @default.
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