Enantioselective Nucleophilic Aromatic Substitution Reaction of Azlactones to Synthesize Quaternary α-Amino Acid Derivatives

AbstractAn asymmetric organocatalytic nucleophilic aromatic substitution reaction of azlactones with electron-deficient aryls was established. A variety of α-aryl α-alkyl α-amino acid esters and peptides were obtained in decent yields and stereoselectivities. A new bifunctional catalytic mode involving charge-transfer interaction and hydrogen bonding is proposed to explain the enantioselectivity.

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One-Pot Synthesis of α-Halo β-Amino Acid Derivatives via the Difunctional Coupling of Ethyl α-Diazoacetate with Silyl Halides and N,O-Acetals or Aromatic Tertiary Amines

Synthesis ◽

10.1055/s-0039-1690864 ◽

2020 ◽

Vol 52 (12) ◽

pp. 1823-1832 ◽

Cited By ~ 1

Author(s):

Norio Sakai ◽

Kazuki Sasaki ◽

Hiroki Suzuki ◽

Yohei Ogiwara

Keyword(s):

Amino Acid ◽

Amino Acid Derivatives ◽

Amino Acid Esters ◽

Tertiary Amines ◽

One Pot ◽

Metal Free ◽

Reaction Intermediate ◽

One Pot Synthesis ◽

Acid Esters ◽

Three Component Coupling

The difunctionalization of ethyl α-diazoacetate (EDA) using silyl halides as a nucleophile and N,O-acetals as an electrophile under metal-free conditions is described. This process undergoes a novel three-component coupling (3-CC) reaction using EDA, which leads to a one-pot preparation of α-halo β-amino acid esters. Also, this protocol could be adapted to accept an electrophile composed of aromatic tertiary amines. In both 3-CC reactions, the key reaction intermediate is an iminium intermediate that can be easily and effectively generated either from N,O-acetals or from aromatic tertiary amines.

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ChemInform Abstract: AN EFFECTIVE SYNTHESIS OF α,β-DEHYDRO-α-AMINO ACID DERIVATIVES FROM N-ACYL-N-HYDROXY-α-AMINO ACID ESTERS

Chemischer Informationsdienst ◽

10.1002/chin.198347121 ◽

1983 ◽

Vol 14 (47) ◽

Author(s):

T. KOLASA

Keyword(s):

Amino Acid ◽

Amino Acid Derivatives ◽

Amino Acid Esters ◽

Effective Synthesis ◽

Acid Esters

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Amino Acid Derivatives, VI [1]: Synthesis, Antiviral, and Antimicrobial Evaluation of α-Amino Acid Esters Bearing a 1,2,3-Triazolo[4,5-d]pyrimidinedione Side Chain

Monatshefte für Chemie - Chemical Monthly ◽

10.1007/s00706-007-0745-8 ◽

2007 ◽

Vol 139 (1) ◽

pp. 61-68 ◽

Cited By ~ 6

Author(s):

Adel A.-H. Abdel-Rahman

Keyword(s):

Amino Acid ◽

Side Chain ◽

Amino Acid Derivatives ◽

Amino Acid Esters ◽

Antimicrobial Evaluation ◽

Acid Esters

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Metal complexes of biologically important ligands, LXXVIII. Synthesis of palladium complexes of ferrocenyl-substituted amino acid derivatives

Canadian Journal of Chemistry ◽

10.1139/v95-143 ◽

1995 ◽

Vol 73 (7) ◽

pp. 1164-1174 ◽

Cited By ~ 33

Author(s):

Doris Freiesleben ◽

Kurt Polborn ◽

Christian Robl ◽

Karlheinz Sünkel ◽

Wolfgang Beck

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Metal Complexes ◽

Palladium Complexes ◽

Amino Acid Derivatives ◽

Amino Acid Esters ◽

X Ray Diffraction ◽

Chelate Complexes ◽

X Ray ◽

Acid Esters

Schiff bases from ferrocene aldehyde and α-amino acidates react with PdCl2 or Na2PdCl4 to give N,O-chelate complexes (2a–e, 3). The related N-ferrocenylmethylen-α-amino acid esters give, with Pd(OAc)2, cyclopalladated acetate-bridged complexes (4a,b). N,O-chelate complexes (5–7) are obtained from Na2PdCl4 with N-ferrocenylmethyl prolinate and-alaninate as well as with N,N-dibenzyl glycinate. The ethyl ester of N,N-dibenzylglycine and Pd(OAc)2 form the cyclopalladated acetate-bridged complex 8, while the ester of N-monobenzylglycine and Na2PdCl4 affords trans-PdCl2(L)2 with a monodentate N-coordinated ligand. The structures of 2a, 4a, 5, 7, and 9 were determined by X-ray diffraction. Keywords: ferrocene, amino acids, palladium(II) complexes, crystal structures.

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