583831-70-3

Upstream product

• 583831-62-3 methyl (1S,2R,4R)-N-benzoyl-2-[(S)-2-thiocarbonyl-1,3-dioxolan-4-yl]-7-azabicyclo[2.2.1]heptane-1-carboxylate 
• 365538-11-0 methyl (1S,2R,4R)-N-benzoyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-azabicyclo[2.2.1]heptane-1-carboxylate 
• 365538-13-2 methyl (1S,2R,4R)-N-benzoyl-2-[(S)-1,2-dihydroxyethyl]-7-azabicyclo[2.2.1]heptane-1-carboxylate 
• 365538-26-7 methyl (1S,2R,4R)-N-benzoyl-2-formyl-7-azabicyclo[2.2.1]heptane-1-carboxylate 
• 583831-63-4 methyl (1S,2S,4R)-N-benzoyl-2-vinyl-7-azabicyclo[2.2.1]heptane-1-carboxylate 

Relevant academic research and scientific papers

Olefination of methyl (1S,2R,4R)-N-benzoyl-2-formyl-7-azabicyclo[2.2.1]heptane-1-carboxylate, a synthetic approach to new conformationally constrained prolines

Wittig olefinations of methyl (1S,2R,4R)-N-benzoyl-2-formyl-7-azabicyclo[2.2.1]heptane-1-carboxylate with several phosphoranes and the Horner-Wittig reaction, using methyl diethylphosphonoacetate, have been tested in order to evaluate their utility in the synthesis of β-substituted conformationally constrained prolines. Subsequent elaboration of the resulting alkenes has provided proline-amino acid chimeras [combinations of proline with other α-amino acids, such as L-norvaline, L-norleucine, L-α-(3-phenylpropyl)glycine or L-homoglutamic acid] with the 7-azabicyclo[2.2.1]heptane skeleton in an enantiomerically pure form.