1369423-51-7Relevant articles and documents
Memory of chirality of tertiary aromatic amide: Application to the asymmetric synthesis of (S)-α-methylDOPA
Mai, Thi Thoa,Viswambharan, Baby,Gori, Didier,Kouklovsky, Cyrille,Alezra, Valerie
, p. 8797 - 8801,5 (2012)
We describe an original asymmetric synthesis of (S)-α-methylDOPA proceeding by the concept of memory of chirality, the only source of chirality being the starting d-alanine. The initial chirality of the amino acid is temporarily transferred to a dynamic axial chirality of a tertiary aromatic amide. The (S)-α-methylDOPA hydrochloride is obtained after four steps with 98% ee.
(S)-ALPHA-FLUOROMETHYLTYROSINE AS DECARBOXYLASE INHIBITORS FOR USE IN THE TREATMENT OF HYPOTENSION
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Paragraph 0159; 0191, (2021/12/31)
Provided are methods of using and drug delivery systems comprising inhibitors of pathogenic, bacterial metabolite production and conjugates of the inhibitors.
Palladium-catalyzed asymmetric benzylation of azlactones
Trost, Barry M.,Czabaniuk, Lara C.
, p. 15210 - 15218 (2013/11/06)
Asymmetric benzylation of prochiral azlactone nucleophiles enables the catalytic introduction of a benzyl group towards the synthesis of α,α-disubstituted amino acids. Herein, we report an enantioselective palladium-catalyzed process using chiral bis(diphenylphosphinobenzoyl)diamine (dppba) ligands. Naphthalene- and heterocycle-based methyl carbonates react with a number of azlactones derived from both natural and unnatural amino acids. Monocyclic benzylic electrophiles, for which the barrier to ionization is higher, must employ a phosphate leaving group in order to react. Reaction conditions for electron-rich and -neutral benzylic electrophiles have been developed, and the scope of the reaction has been explored with respect to both reaction partners. The high levels of asymmetric induction, as well as the reactivity pattern of the electrophiles, suggest an η3-benzyl intermediate that arises through two distinct pathways. Attack on benzyl: Palladium-catalyzed asymmetric benzylation methodology is demonstrated on prochiral azlactone nucleophiles. The use of naphthyl, heterocyclic, and monocyclic benzylic electrophiles demonstrates the wide reaction scope (see scheme; Cp=cyclopentadienyl). The benzylation products are readily converted into enantioenriched α,α-disubstituted amino acids.