78553-48-7Relevant academic research and scientific papers
Enantioselective Synthesis of α-Allyl Amino Esters via Hydrogen-Bond-Donor Catalysis
Bendelsmith, Andrew J.,Kim, Seohyun Chris,Wasa, Masayuki,Roche, Stéphane P.,Jacobsen, Eric N.
, p. 11414 - 11419 (2019/08/20)
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.
Enantiomerically enriched allylglycine derivatives through the catalytic asymmetric allylation of iminoesters and iminophosphonates with allylsilanes
Kiyohara, Hiroshi,Nakamura, Yoshitaka,Matsubara, Ryosuke,Kobayashi, Shu
, p. 1615 - 1617 (2008/02/02)
(Chemical Equation Presented) α-Amino acid derivatives are obtained in high yields through the catalytic enantioselective allylation of iminoesters using environmentally benign allylsilanes as nucleophiles in the presence of a copper complex prepared from
SYNTHESIS OF NICOTIANAMINE AND A RELATED COMPOUND, DERIVATIVES OF AZETIDINE-2-CARBOXYLIC ACID
Fushiya, Shinji,Nakatsuyama, Shuichi,Sato, Yoshikazu,Nozoe, Shigeo
, p. 819 - 822 (2007/10/02)
The synthesis of nicotianamine (1) and a related compound (2) - amino acid derivatives having the azetidine ring - was achieved by reductive coupling of L-aspartic-β-semialdehyde derivatives with L-azetidine-2-carboxylic acid methyl ester.
