188200-10-4

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 188200-09-1 (1R,2S)-N-Benzyl-2,3-dibenzyloxy-1-phenyl-1-propylamine 
• 100-58-3 phenylmagnesium bromide 
• 238401-87-1 (R)-2,3-di-O-benzylglyceraldehyde N-benzylimine 

Downstream Products

• 33125-05-2 Boc-D-Phg-OH 
• 875-74-1 (R)-phenylglycine 
• 188200-11-5 (2S,3R)-3-((tert-butoxycarbonyl)amino)-3-phenyl-1,2-propanediol 

Relevant academic research and scientific papers

Reversal of the stereochemical course of the addition of phenylmagnesium bromide to N-benzylimines derived from R-glyceraldehyde depending on the O-protecting group and its application to the synthesis of both enantiomers of phenylglycine

The N-Benzyl imines derived from 2,3-di-O-benzyl-D-glyceraldehyde and 2,3-di-O-isopropylidene-D-glyceraldehyde reacted with phenylmagnesium bromide to afford fully protected aminodiols with total diastereoselectivity. The stereochemical course of the addition reaction depends on the nature of the O-protecting group. These compounds can be easily transformed to enantiomerically pure (R) and (S)α-phenylglycine.