92085-86-4

Upstream product

• 27200-84-6 methyl triphenylphosphonium bromide 
• 79069-54-8 (S)-2-(t-butoxycarbonylamino)-3-phenylmetoxy-1-propanal 
• 100-39-0 benzyl bromide 
• 89985-86-4 (R)-2-(N-tert-butoxycarbonylamino)-3-buten-1-ol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 4248-19-5 tert-butyl carbazate 
• 1169852-11-2 tert-butyl (E)-4-benzyloxybut-2-enyl carbonate 
• 51779-32-9 iminodicarboxylic acid di-tert-butyl ester 

Downstream Products

• 114671-11-3 (4R^*,5S^*)-4-(benzyloxymethyl)-5-vinyl-2-oxazolidinone 
• 114671-11-3 (4R^*,5R^*)-4-(benzyloxymethyl)-5-vinyl-2-oxazolidinone 
• 114671-07-7 N-(tert-butyldimethylsilyloxycarbonyl)-2-amino-1-(benzyloxy)-5-chloro-3-pentene 
• 124754-92-3 ((E)-(R)-1-Benzyloxymethyl-4-hydroxy-but-2-enyl)-carbamic acid tert-butyl ester 
• 124754-55-8 (2R)-N-(tert-butoxycarbonyl)-2-amino-1-(benzyloxy)-5-chloro-3-pentene 
• 124754-86-5 ((E)-(R)-1-Benzyloxymethyl-4-oxo-but-2-enyl)-carbamic acid tert-butyl ester 
• 97682-96-7 (R)-1-(benzyloxy)but-3-en-2-amine 
• 92085-90-0 threo-N-Boc-O-benzyl-serine epoxide 
• 92085-90-0 erythro-N-Boc-O-benzyl-serine epoxide 
• 79069-54-8 (S)-2-(t-butoxycarbonylamino)-3-phenylmetoxy-1-propanal 

Relevant academic research and scientific papers

Iridium-catalyzed asymmetric allylic substitutions with bulky amines/oxidative double bond cleavage - Entry into the reetz synthesis of amino alcohols

Branched allylic amines were prepared by Ir-catalyzed enantioselective allylic aminations with the bulky N-nucleophiles HN(Boc)2 and HNBn2. The products were transformed into N-protected amino aldehydes, which were either reduced or coupled diastereoselectively with organometallic compounds to give vicinal amino alcohols. A formal synthesis of the neurokinin receptor antagonist (+)-L-733060 was carried out as an application. Ir-catalyzed enantioselective allylic aminations with bulky N-nucleophiles HN(Boc)2 and HNBn2 gave N-protected allylic amines, which were transformed into N-protected chiral amino aldehydes. These are useful chiral building blocks as previously demonstrated by Reetz et al. A formal synthesis of the neurokinin receptor antagonist (+)-L-733060 was carried out as an application.

Direct, intermodular, enantioselective, iridium-catalyzed allylation of carbamates to form carbamate-protected, branched allylic amines

The direct reaction between carbamates and achiral allylic carbonates to form branched, conveniently protected primary allylic amines with high regioseiectivity and enantioselectivity Is reported. This process occurs without base or with 0.5 equiv K3PO4 In the presence of a metalacyclic iridium catalyst containing a labile ethylene ligand. The reactions of aryl-, heteroaryl-, and alkyl-substituted allylic carbonates with BocNH 2, FmocNH2, CbZNH2, TrocNH2, TeocNH2, and 2-oxazolidinone occur In good yields, with high selectivity for the branched isomer and high enantioselectivities (98% average ee).

Synthesis of enantiomerically pure (+)- and (-)-protected 5-aminomethyl-1,3-oxazolidin-2-one derivatives from allylamine and carbon dioxide

The stereoselective synthesis of enantiomerically pure (5R)- and (5S)-aminomethyl-oxazolidinones with different protecting groups have been carried out from an allyl amine as the source of the carbon backbone. The key reaction is the high yield iodiocyclization of enantiomerically pure allylphenethyl amine in the presence of carbon dioxide.

A Synthesis of Protected Aminoalkyl Epoxides from α-Amino Acids

The synthesis of alkylamino epoxides C is presented.Key steps include the synthesis of amino aldehyde 5 by reduction (DIBAH) of ester 3 or by oxidation of N-protected amino alcohol 4, both edducts of which are derived from amino acids.A study of the olefination of aldehyde 5 with unstabilized ylides is presented, and protected allylic amino 6, obtained in good to excellent optical purity, is oxidized (MCPBA) to epoxide C.Threo selectivity is observed in the epoxidation reaction.