844865-30-1

Upstream product

• 648433-21-0 (2R,3S)-3-exo-benzyloxycarbonyl-7-oxabicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid 
• 844865-25-4 (1R,2S,3R,4S)-3-Azidocarbonyl-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid benzyl ester 
• 844865-29-8 (1R,2R,3R,4S)-3-[Benzyl-(4-methoxy-benzyloxycarbonyl)-amino]-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid benzyl ester 
• 844865-27-6 (1S,2S,3R,4R)-5,6-Dibromo-3-(4-methoxy-benzyloxycarbonylamino)-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester 
• 844865-28-7 (1R,2S,3R,4S)-3-(4-Methoxy-benzyloxycarbonylamino)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid benzyl ester 
• 844865-26-5 (1S,2S,3R,4R)-3-Azidocarbonyl-5,6-dibromo-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester 
• 6118-51-0 exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride 

Downstream Products

• 1026575-47-2 (E)-3-{Benzyl-[(S)-benzylcarbamoyl-(4-chloro-phenyl)-methyl]-amino}-acrylic acid methyl ester 
• 1027155-15-2 (E)-3-{Benzyl-[(S)-benzylcarbamoyl-(3-methoxy-phenyl)-methyl]-amino}-acrylic acid methyl ester 
• 1027920-84-8 (E)-3-[Benzyl-((S)-1-benzylcarbamoyl-2-phenyl-ethyl)-amino]-acrylic acid methyl ester 
• 1027081-65-7 (E)-3-[Benzyl-((S)-1-benzylcarbamoyl-propyl)-amino]-acrylic acid methyl ester 
• 844865-42-5 N-benzyl-2-benzylamino-2-(4-chloro-phenyl)-acetamide 
• 844865-41-4 N-benzyl-2-benzylamino-2-(3-methoxy-phenyl)-acetamide 
• 844865-43-6 (S)-N-benzyl-2-(benzylamino)-3-phenylpropanamide 
• 844865-39-0 (S)-2-Benzylamino-4-methyl-pentanoic acid benzylamide 
• 844865-40-3 N-benzyl-2-benzylamino-butyramide 

Relevant academic research and scientific papers

Straightforward stereoselective synthesis of polyfunctionalised cyclohexenols using a multicomponent approach

An intramolecular Ugi 5-centre-4-component reaction (U-5C-4CR) followed by a palladium-catalysed ring-opening has been employed to transform oxabicycloheptene-based β-amino acids into two families of regioisomeric polyfunctionalised cyclohexenols. The whole process is completely stereoselective and enantiomerically pure products are obtained in high overall yields.

A novel highly selective chiral auxiliary for the asymmetric synthesis of L- and D-α-amino acid derivatives via a multicomponent ugi reaction

(Chemical Equation Presented) This paper describes the synthesis of a bicyclic β-amino acid scaffold in both pure enantiomeric forms and its application as chiral auxiliary in an intramolecular version of the Ugi multicomponent reaction (U-5C-4CR) to prepare α-amino acid derivatives of both D- and L-series in a straightforward and very stereoselective manner. The mild conditions required for the Ugi condensation and for the removal of the chiral auxiliary make this method very attractive to prepare a wide range of differently structured N-alkylated and unalkylated amino acid derivatives.