87900-12-7

Upstream product

• 87974-74-1 2-[(1R,2R,5R)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-pentanoic acid methyl ester 
• 74-88-4 methyl iodide 
• 87974-74-1 2-[(1S,2S,5S)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3Z)-ylideneamino]-pentanoic acid methyl ester 
• 87974-73-0 2-[(1R,2R,5R)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-propionic acid methyl ester 
• 107-08-4 1-iodo-propane 
• 87974-73-0 2-[(1S,2S,5S)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3Z)-ylideneamino]-propionic acid methyl ester 
• 92261-70-6 (R)-2-[(1S,2S,5S)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-2-methyl-pentanoic acid methyl ester 

Relevant academic research and scientific papers

SYNTHESE ASYMETRIQUE D'ACIDES AMINES α-DISUBSTITUES

α-Disubstituted amino acids are prepared with good optical yields by enantioselective substitution using Schiff bases between α-monosubstituted amino acids and (S,S,S) or (R,R,R)-2-hydroxypinan-3-one as chiral reagent.The configuration of these acids is found to be dependent on the shielding effect of their aliphatic chain in the intermediary Schiff dianion.

REACTIONS OF SCHIFF BASE ANIONS WITH ELECTROPHILES: ROLE OF THE INITIAL STEREOCHEMISTRY

It is shown that the reactivity towards electrophiles of diastereomeric Schiff bases of *R and *S valine, leucine, phenylalanine and norvaline methyl esters with (1S,2S,5S) or (1R,2R,5R) 2-hydroxy 3-pinanone, is highly dependent on the stereochemistry of the starting product.