474558-70-8Relevant articles and documents
Ring-closing metathesis of chiral allylamines. Enantioselective synthesis of (2S,3R,4S)-3,4-dihydroxyproline
Martin, Ruben,Alcon, Montserrat,Pericas, Miquel A.,Riera, Antoni
, p. 6896 - 6901 (2002)
The ring-closing metathesis (RCM) of two types of unsaturated chiral allylamines III, easily available from enantiomerically enriched epoxy alcohols, has been studied. Fully protected allylamines IIIa [1R = CH2-(CH2)n-CH=CH2; 2R = Boc; 3R = PMB] have been prepared from unsaturated 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 to provide either cyclic allylamine I or II. The synthetic potential of these intermediates has been demonstrated by the enantioselective synthesis of (2S,3R,4S)-3,4-dihydroxyproline.