474558-80-0

Upstream product

• 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 
• 100-52-7 benzaldehyde 
• 735334-59-5 (S)-N-(1-phenyl-2-propenyl)allylamine 

Downstream Products

• 474558-83-3 (2R,3R,4S)-(-)-N-tert-butoxycarbonyl-3,4-dihydroxy-2-phenyl-pyrrolidine isopropylidene acetal 
• 474558-82-2 (2R,3R,4S)-N-tert-butoxycarbonyl-3,4-dihydroxy-2-phenylpyrrolidine 
• 316813-68-0 (2S)-N-tert-butoxycarbonyl-2-phenyl-2,5-dihydropyrrole 

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.

Enantioselective synthesis of 2-substituted-N-Boc-Δ-4,5-piperidines

The title compounds were prepared through a synthetic sequence involving: (i) a reaction of the condensation product between an enantiopure β-amino alcohol and an aldehyde with allylmagnesium chloride; (ii) an N-allylation of the resulting secondary amine; (iii) a chemoselective cleavage of the β-amino alcohol residue; and (iv) a protection of the secondary amine followed by a ring closing metathesis. The advantageous use of (1R,2S)-norephedrine was demonstrated in these syntheses.