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À propos de : Ring-Closing Metathesis of Chiral Allylamines. EnantioselectiveSynthesis of (2S,3R,4S)-3,4-Dihydroxyproline        

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  • Ring-Closing Metathesis of Chiral Allylamines. EnantioselectiveSynthesis of (2S,3R,4S)-3,4-Dihydroxyproline
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  • The ring-closing metathesis (RCM) of two types of unsaturated chiral allylamines III, easilyavailable from enantiomerically enriched epoxy alcohols, has been studied. Fully protectedallylamines IIIa [1R = CH2−(CH2)n−CHCH2; 2R = Boc; 3R = PMB] have been prepared fromunsaturated epoxy alcohols, whereas bis-allylamines IIIb (1R = Ph, 2R = allyl,3R = Boc or PMB)have been prepared from 2,3-epoxy-3-phenylpropanol. Both types have been subjected to RCM toprovide either cyclic allylamine I or II. The synthetic potential of these intermediates has beendemonstrated by the enantioselective synthesis of (2S,3R,4S)-3,4-dihydroxyproline.
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