19490-53-0

Upstream product

• 108-24-7 acetic anhydride 
• 911666-02-9 N-((1R,2R)-2-hydroxy-1-methoxymethyl-2-phenyl-ethyl)-phthalimide 
• 51293-45-9 (R)-2-(isoindolin-2-yl)-3-methoxypropanoic acid 
• 51293-45-9 O-methyl-N,N-phthaloyl-DL-serine 
• 19437-22-0 N-((R)-1-methoxymethyl-2-oxo-2-phenyl-ethyl)-phthalimide 
• 136918-14-4 phthalimide 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 16277-67-1 (Z)-(3-methoxyprop-1-en-1-yl)benzene 
• 85083-55-2 2-bromo-3-methoxy-1-phenyl-propan-1-one 
• 1074-82-4 potassium phtalimide 
• 19437-22-0 N-(1-methoxymethyl-2-oxo-2-phenyl-ethyl)-phthalimide 
• 71-43-2 benzene 

Downstream Products

• 119-62-0 (+/-)-threo-1-(4-nitro-phenyl)-2-amino-1,3-propanediol 
• 63457-14-7 (1RS,2RS)-2-amino-3-methoxy-1-(4-nitro-phenyl)-propan-1-ol 
• 57302-63-3 (1RS,2RS)-2-(2,2-dichloro-acetylamino)-3-methoxy-1-(4-nitro-phenyl)-propan-1-ol 
• 63457-14-7 (1RS,2SR)-2-amino-3-methoxy-1-(4-nitro-phenyl)-propan-1-ol 
• 104741-18-6 (1SR,2SR)-2-acetylamino-3-methoxy-1-(4-nitro-phenyl)-propan-1-ol 
• 102003-47-4 (1RS,2RS)-1-acetoxy-3-methoxy-1-(4-nitro-phenyl)-2-phthalimido-propane 

Relevant academic research and scientific papers

Highly regioselective Pd-catalyzed intermolecular aminoacetoxylation of alkenes and evidence for cis-aminopalladation and SN2 C-O bond formation

Synthetic methods that achieve oxidative 1,2-difunctionalization of alkenes are very powerful in organic chemistry. Here we report the first examples of intermolecular Pd-catalyzed aminoacetoxylation of alkenes with phthalimide as the nitrogen source and PhI(OAc)2 as the stoichiometric oxidant and source of acetate. These reactions are highly regio- and diastereoselective, and mechanistic studies reveal that the reaction proceeds via cis-aminopalladation of the alkene followed by oxidative cleavage of the intermediate Pd-C bond with inversion of stereochemistry. Copyright

Palladium-catalyzed intermolecular aminoacetoxylation of alkenes and the influence of PhI(OAc)2 on aminopalladation stereoselectivity

A modified protocol has been identified for Pd-catalyzed intermolecular aminoacetoxylation of terminal and internal alkenes that enables the alkene to be used as the limiting reagent. The results prompt a reassessment of the stereochemical course of these reactions. X-ray crystallographic characterization of two of the products, together with isotopic labeling studies, show that the amidopalladation step switches from a cis-selective process under aerobic conditions to a trans-selective process in the presence of diacetoxyiodobenzene.