Convenient Methods for the Synthesis of Chiral Amino Alcohols and Amines

Periasamy, Muthu; Gurubrahamam, Ramani; Sanjeevakumar, Nalluri; Dalai, Manasi; Alakonda, Laxhmaiah; Reddy, Polimera Obula; Suresh, S.; Satishkumar, Sakilam; Padmaja, Meduri; Reddy, Meda Narsi; Suresh, Surisetti; Anwar, Shaik; Muthukumaragopal, Gopal P.; Vairaprakash, Pothiappan; Seenivasaperumal, M.

doi:10.2533/chimia.2013.23

Cited by 22 publications

(12 citation statements)

References 26 publications

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“…All experiments were monitored by thin layer chromatography (TLC) using UV light as visualizing agent. 1 H NMR (400 MHz), 13 C NMR (101 MHz), and 19 F NMR (376 MHz) were measured on Bruker AVANCE III-400 spectrometer. Melting points are uncorrected.…”

Section: General Informationmentioning

confidence: 99%

“…[2][3][4][5][6] Subsequently, the development of advanced asymmetric methodologies for scalable synthesis of structurally diverse AAs is currently in high demand. [7][8][9][10][11][12][13][14][15][16][17][18] For quite some time, our groups were interested in pursuing new synthetic approaches for preparation of sterically constrained, 19,20 phosphorus, 21,22 and fluorine-containing [23][24][25] AAs. One of the most methodologically prolific directions, inspired by the seminal work by Belokon, 26,27 has been the chemistry of Ni(II) complexes of AAs derived Schiff bases (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

“…H NMR (400 MHz),13 C NMR (101 MHz), and 19 F NMR (376 MHz) were measured on Bruker AVANCE III-400 spectrometer. Melting points are uncorrected.…”

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confidence: 99%

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Axially chiral Ni(II) complexes of α‐amino acids: Separation of enantiomers and kinetics of racemization

et al. 2018

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Herein we present design, synthesis, chiral HPLC resolution, and kinetics of racemization of axially chiral Ni(II) complexes of glycine and di-(benzyl)glycine Schiff bases. We found that while the ortho-fluoro derivatives are configurationally unstable, the pure enantiomers of corresponding axially chiral ortho-chloro-containing complexes can be isolated by preparative HPLC and show exceptional configurational stability (t from 4 to 216 centuries) at ambient conditions. Synthetic implications of this discovery for the development of new generation of axially chiral auxiliaries, useful for general asymmetric synthesis of α-amino acids, are discussed.

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Section: General Informationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Axially chiral Ni(II) complexes of α‐amino acids: Separation of enantiomers and kinetics of racemization

et al. 2018

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“…In fact, over 30% of small-molecule drugs contain residues of tailor-made AAs [ 2 , 6 , 7 , 8 ], while peptidomimetics and peptide class drugs are fully based on AAs [ 9 , 10 , 11 , 12 ]. Consequently, the interest in development of synthetic approached for the preparation of tailor-made AA is at an all-time high [ 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 ]. Over the last decade, transformations of chiral Ni(II) complexes of Schiff bases derived from tridentate ligands and AAs ( Scheme 1 ), have emerged as a leading methodology for asymmetric synthesis of tailor-made AAs [ 23 , 24 ].…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Synthesis of Tailor-Made Amino Acids Using Chiral Ni(II) Complexes of Schiff Bases. An Update of the Recent Literature

et al. 2020

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Tailor-made amino acids are indispensable structural components of modern medicinal chemistry and drug design. Consequently, stereo-controlled preparation of amino acids is the area of high research activity. Over last decade, application of Ni(II) complexes of Schiff bases derived from glycine and chiral tridentate ligands has emerged as a leading methodology for the synthesis of various structural types of amino acids. This review article summarizes examples of asymmetric synthesis of tailor-made α-amino acids via the corresponding Ni(II) complexes, reported in the literature over the last four years. A general overview of this methodology is provided, with the emphasis given to practicality, scalability, cost-structure and recyclability of the chiral tridentate ligands.

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“…Synthesis of fluorinated AAs is part of a more general field of asymmetric synthesis of tailor-made amino acids. Therefore, some recent advances, covered by the excellent review articles, should be mentioned [52][53][54][55][56][57][58][59][60][61].…”

Section: Introductionmentioning

confidence: 99%

Preparative Method for Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid

et al. 2019

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Enantiomerically pure derivatives of 2-amino-4,4,4-trifluorobutanoic acid are in great demand as bioisostere of leucine moiety in the drug design. Here, we disclose a method specifically developed for large-scale (>150 g) preparation of the target (S)-N-Fmoc-2-amino-4,4,4-trifluorobutanoic acid. The method employs a recyclable chiral auxiliary to form the corresponding Ni(II) complex with glycine Schiff base, which is alkylated with CF3–CH2–I under basic conditions. The resultant alkylated Ni(II) complex is disassembled to reclaim the chiral auxiliary and 2-amino-4,4,4-trifluorobutanoic acid, which is in situ converted to the N-Fmoc derivative. The whole procedure was reproduced several times for consecutive preparation of over 300 g of the target (S)-N-Fmoc-2-amino-4,4,4-trifluorobutanoic acid.

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Convenient Methods for the Synthesis of Chiral Amino Alcohols and Amines

Cited by 22 publications

References 26 publications

Axially chiral Ni(II) complexes of α‐amino acids: Separation of enantiomers and kinetics of racemization

Axially chiral Ni(II) complexes of α‐amino acids: Separation of enantiomers and kinetics of racemization

Asymmetric Synthesis of Tailor-Made Amino Acids Using Chiral Ni(II) Complexes of Schiff Bases. An Update of the Recent Literature

Preparative Method for Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid

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