104473-51-0Relevant articles and documents
Asymmetric Mannich synthesis of α-amino esters by anion-binding catalysis
Wasa, Masayuki,Liu, Richard Y.,Roche, Stéphane P.,Jacobsen, Eric N.
, p. 12872 - 12875 (2014)
We report a scalable, one-pot Mannich route to enantioenriched α-amino esters by direct reaction of α-chloroglycine ester as a practical imino ester surrogate. The reaction is promoted by a chiral aminothiourea, which is proposed to operate cooperatively
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.
supporting information, 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.
A chiral α - amino acid derivative and its preparation method (by machine translation)
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Paragraph 0093; 0096; 0097, (2018/01/03)
The invention discloses a chiral α - amino acid derivative and its preparation method. The invention α - chiral amino acid derivatives, its structural formula shown in formula I: Its preparation method, comprises the following steps: with the carbonyl compound to the N, O - acetal of the mixture with a chiral primary uncle diamine organic small molecule catalyst, strong and weak acid mixing, reaction, to obtain the chiral α - amino acid compounds; the carbonyl compound including aldehyde and/or ketone. The invention chiral α - amino acid ester compound having a simple structure of the chiral primary uncle diamine organic small molecule catalyst catalytic, solvent-free, one-step synthesis, simple, high-efficiency. (by machine translation)