1431561-60-2

Upstream product

• 108-86-1 bromobenzene 
• 62965-35-9 N-tert-butyloxycarbonyl-L-tert-leucine 
• 174311-02-5 2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 1431561-56-6 1-((S)-3,3-dimethyl-1-oxo-1-((R)-2-phenylpyrrolidin-1-yl)butan-2-yl)-3-((1R,2R)-2-(2-methyl-5-phenyl-1H-pyrrol-1-yl)cyclohexyl)thiourea 

Relevant academic research and scientific papers

Enantioselective Synthesis of α-Allyl Amino Esters via Hydrogen-Bond-Donor Catalysis

We report a chiral-squaramide-catalyzed enantio- and diastereoselective synthesis of α-allyl amino esters. The optimized protocol provides access to N-carbamoyl-protected amino esters via nucleophilic allylation of readily accessible α-chloro glycinates. A variety of useful α-allyl amino esters were prepared, including crotylated products bearing vicinal stereocenters that are inaccessible through enolate alkylation, with high enantioselectivity (up to 97% ee) and diastereoselectivity (>10:1). The reactions display first-order kinetic dependence on both the α-chloro glycinate and the nucleophile, consistent with rate-limiting C-C bond formation. Computational analysis of the uncatalyzed reaction predicts an energetically inaccessible iminium intermediate, and a lower energy concerted SN2 mechanism.