777889-56-2

Upstream product

• 105-36-2 ethyl bromoacetate 
• 175355-34-7 N-(cyclohexylmethylene)-4-methylbenzenesulfonamide 
• 70-55-3 toluene-4-sulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant academic research and scientific papers

β-Amino esters from the reductive ring opening of aziridine-2-carboxylates

A general study is undertaken to examine the scope of the reductive ring opening of aziridine-2-carboxylates with samarium diiodide. The competition between C-C and C-N bond cleavage is examined as a function of the nature of the N-substituent of the aziridine, the nature of the substituent in the 3-position of the aziridine, and whether the substituent in the 3-position is in a cis or trans relationship with the carboxylate in the 2-position. The desired C-N bond cleavage leads to β-amino esters that are the predominant products for most aziridines with an N-activating group. However, C-C cleavage products are observed with an aryl group in the 3-position; this can be particularly pronounced with cis-aziridines where a nearly equal mixture of the two is observed. Exclusive formation of the C-N cleavage product is observed for all aziridines with the strongly N-activating p-toluene sulfonate group. Similarly high selectivity is observed for the 2-trimethylsilylethyl sulfonate group (SES), which is easier to remove. The utility of these methods is illustrated in the synthesis of protected forms of (R)-β3-DOPA and l-DOPA from the same aziridine, the former by SmI2-mediated reductive opening at C-2 and the latter by palladium-mediated reductive opening at C-3.

Aza-Reformatsky reaction promoted by catalytic samarium diiodide: Synthesis of β-amino esters or amides

The synthesis of β-amino esters or amides has been achieved from moderate to high yields from the reaction of imines and α-halo esters or amides promoted by catalytic amounts of samarium diiodide in the presence of magnesium turnings as co-reductant. A me

The use of samarium enolates, A novel alternative in the addition reactions to imines. Synthesis of 3-amino esters, amides and enantiopure 3,4-diamino esters

An efficient reaction of tosylimines with a range of samarium enolates (derived from esters, and amides) is reported. The reaction with the α-dibenzylamino-N-tert-butanesulfinimine derived from chiral phenylalaninal afforded the corresponding enantiopure

The addition reaction of samarium enolates and 2-haloenolates derived from esters, and amides to imines. totally stereoselective synthesis of enantiopure 3,4-diamino esters or amides

The addition reaction of samarium enolates and 2-haloenolates derived from esters and amides to imines takes place in an efficient manner. A novel protocol to perform the addition reaction of samarium enolates derived from esters or amides to chiral 2-ami