474558-82-2

Upstream product

• 316813-68-0 (2S)-N-tert-butoxycarbonyl-2-phenyl-2,5-dihydropyrrole 
• 474558-80-0 (1S)-N-allyl-N-(tert-butoxycarbonyl)-1-phenylallylamine 
• 474558-78-6 Allyl-((1R,2R)-2,3-dihydroxy-1-phenyl-propyl)-carbamic acid tert-butyl ester 
• 474558-77-5 (2R,3R)-3-allylamino-3-phenylpropane-1,2-diol 
• 21915-53-7 (2R,3S)-(3-phenyloxiran-2-yl)methanol 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 474558-83-3 (2R,3R,4S)-(-)-N-tert-butoxycarbonyl-3,4-dihydroxy-2-phenyl-pyrrolidine isopropylidene acetal 

Relevant academic research and scientific papers

Ring-closing metathesis of chiral allylamines. Enantioselective synthesis of (2S,3R,4S)-3,4-dihydroxyproline

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.