189516-44-7

Upstream product

• 54125-02-9 danishefsky's diene 
• 238401-87-1 (R)-2,3-di-O-benzylglyceraldehyde N-benzylimine 

Downstream Products

• 189516-46-9 (R)-8-Benzyl-7-((S)-1,2-bis-benzyloxy-ethyl)-1,4-dioxa-8-aza-spiro[4.5]decane 
• 189516-45-8 (R)-1-Benzyl-2-((S)-1,2-bis-benzyloxy-ethyl)-piperidin-4-one 

Relevant academic research and scientific papers

Asymmetric hetero Diels-Alder reaction of N-benzylimines derived from R-glyceraldehyde: A new approach to homochiral piperidine building blocks and its application to the synthesis of (2R)-4-oxopipecolic acid

The N-Benzyl imine derived from 2,3-di-O-benzyl-D-glyceraldehyde reacts with Danishefsky's diene to afford the corresponding hetero Diels-Alder adduct with a high diastereoselectivity. This compound can be transformed to enantiomerically pure (2R)-4-oxopi

Study of the reaction of imines derived from (R)-glyceraldehyde with Danishefsky's diene

N-Benzylimines derived from conveniently protected (R)-glyceraldehyde underwent diastereoselective tandem Mannich-Michael reaction with Danishefsky's diene in the presence of Lewis acids. The temperature, catalyst and solvent dependence of the product rat