219598-57-9

Upstream product

• 25726-04-9 phenylglyoxylyl chloride 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 

Downstream Products

• 219598-69-3 (S)-2-hydroxymethyl-N-((R)-2-hydroxy-2-phenyl)pentanoylpyrrolidine 
• 219598-68-2 (S)-2-hydroxymethyl-N-((R)-2-hydroxy-2-phenyl)-butanoylpyrrolidine 
• 110457-29-9 (S)-2-hydroxymethyl-N-((R)-2-hydroxy-2-phenyl)propanoylpyrrolidine 
• 110457-30-2 (S)-2-hydroxymethyl-N-((S)-2-hydroxy-2-phenyl)propanoylpyrrolidine 
• 102061-04-1 (2S)-2-(hydroxymethyl)-1-[(2R)-2-hydroxy-2-phenylacetyl]pyrrolidine 
• 102061-02-9 (S)-2-hydroxymethyl-N-((R)-2-hydroxy-2-phenyl)-acetyl pyrrolidine 
• 219598-58-0 (S)-2-hydroxymethyl-N-benzoylformyl pyrrolidine 

Relevant academic research and scientific papers

Asymmetric reactions of α-ketoacid-derived hemiacetals: Stereoselective synthesis of α-hydroxy acids

N-Acylation of prolinol with α-ketoacid chlorides results in concomitant hemiacetalization of the α-keto amide by the prolinol hydroxyl group. (R) or (S) α-hydroxy acids are obtained with good enantiomeric excess by stereodivergent reduction of these hemiacetals. Reaction with Grignard reagents at ambient temperature furnishes (R) α-alkyl mandelic acids with good stereoselectivity.

Stereodivergent Approach to α-Hydroxy Acids Involving Substrate Directed Reduction of α-Keto Amides

Substrate directed reduction of 'S'-2-hydroxymethylpyrrolidine derived α-keto amides with tetramethylammonium triacetoxyborohydride proceeds with good stereoselectivity at room temperature.A reversal of stereoselectivity is observed in reductions with conventional borohydride reducing agents in protic solvents.