752212-30-9

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 148312-55-4 tert-butyl thiazolidine-3-carboxylate 
• 100-52-7 benzaldehyde 
• 108-24-7 acetic anhydride 
• 750645-80-8 2-(hydroxy-phenyl-methyl)-thiazolidine-3-carboxylic acid tert-butyl ester 

Downstream Products

• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 
• 83461-64-7 (R)-α-acetoxyphenylacetaldehyde 

Relevant academic research and scientific papers

Enantioselective reaction of α-lithiated thiazolidines as new chiral formyl anion equivalents

The reaction of lithiated N-Boc-thiazolidine and N-Boc-benzothiazolidine with benzophenone in the presence of (-)-sparteine afforded the products with up to 97% ee and 93% ee, respectively. The reaction with various aromatic and aliphatic aldehydes also afforded the products with high enantioselectivity and moderate diastereoselectivity. Each diastereomer could be converted to optically active diols. Consequently, lithiated N-Boc-thiazolidine and N-Boc-benzothiazolidine serve as chiral formyl anion equivalents. The reaction was confirmed to proceed through a dynamic thermodynamic resolution pathway.

Highly enantioselective reaction of lithiated N-Boc-thiazolidine: A new chiral formyl anion equivalent

Reaction of lithiated N-Boc-thiazolidine 1 with various aldehydes in the presence of (-)-sparteine afforded the products with up to 93% ee. The reaction was confirmed to proceed through a dynamic thermodynamic resolution pathway. Each diastereomeric alcohol could be converted to the corresponding optically active 1,2-ethanediols.