140867-29-4

Upstream product

• 2207-27-4 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene 
• 140867-28-3 (+/-)-N-benzoyl-α-vinylalaninol 
• 74761-84-5 (+/-)-N-benzoyl-α-vunylalanine methyl ester 

Downstream Products

• 140867-31-8 (1R*,4S*,5S*,2'R*)-7,7-dimethoxy-1,2,3,4-tetrachloro-5-<2'-(2'-amino-1'-benzyloxy)-propyl>-bicyclo<2.2.1>hept-2-ene 
• 140867-31-8 (1R*,4S*,5S*,2'S*)-7,7-dimethoxy-1,2,3,4-tetrachloro-5-<2'-(2'-amino-1'-benzyloxy)-propyl>-bicyclo<2.2.1>hept-2-ene 
• 140867-33-0 (1R*,2R*,3S*,6S*,7S*,8S*)-6-benzamido-6-methyl-1,2,8-trichloro-3,9,9-trimethoxy-4-oxatricyclo<5.2.1.0^3,8>decane 

Relevant academic research and scientific papers

A new retro-aza-ene reaction: Formal reductive amination of an α-keto acid to an α-amino acid

Two diastereomeric reductive amination reagents, 1a and 1b, were synthesized. Each reagent was condensed with ethyl pyruvate as a model α-keto acid. Flash vacuum pyrolysis of the pyruvate adducts, 10a and 10b, results in cheleotropic elimination of CO, followed by a new type of retro-aza-ene reaction. A molecule of benzene and a protected alanine derivative, 11, are produced in the retro-ene reaction. This sequence constitutes the first formal more readily than distereomer 10a, indicating that an exo transition state is preferred over an endo transition state for this particular retro-aza-ene reaction.