174591-36-7

Upstream product

• 84049-31-0 (2R,4S)-3-aza-2-methyl-4-phenyl-ethylpentanoate 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 217952-09-5 (R)-2-[((S)-2-Acetoxy-propionyl)-((S)-1-phenyl-ethyl)-amino]-propionic acid ethyl ester 
• 174591-35-6 (6S,1'S)-6-methyl-4-(1'-phenylethyl)-1,4-morpholine-2,5-dione 
• 74-88-4 methyl iodide 

Downstream Products

• 338-69-2 D-Alanine 

Relevant academic research and scientific papers

Stereoselective synthesis of uncommon α,α'-dialkyl-α- aminoacids. Part 1

The alkylation of the diastereomeric mixture of chiral morpholinone derivatives 4 and 5 occurs with good yield and trans induction. Cleavage of the alkylated products 6a,b,c,e gives enantiomerically pure uncommon (and sterically constrained) α,α'-dialkyl-α-aminoacids. The absolute configuration of the new stereocentres of 4, 5, 6 and 7 has been assigned on the basis of the 1H-NMR spectra and NOE measurements.

Enantioselective Synthesis of (R)- and (S)-α-Aminoacids using (6S)- and (6R)-6-Methyl-morpholine-2,5-dione Derivatives

The alkylation of both 3 and 4 gives exclusively the trans derivatives 5 and 6, respectively, with >98% diastereoselectivity. Cleavage of the morpholine-2,5-dione ring of 5 and 6 leads to enantiomerically pure (S)- and (R)-α-aminoacids, respectively. The configurations of stereogenic centers introduced on 3, 4, 5 and 6 have been assigned on the basis of the 1H-NMR data, conformational analysis and nOe measurements.