Asymmetric Synthesis of α-Amino Acids by Organocatalytic Biomimetic Transamination

Kang, Qi‐Kai; Selvakumar, Sermadurai; Maruoka, Keiji

doi:10.1021/acs.orglett.9b00588

Cited by 16 publications

(21 citation statements)

References 35 publications

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“…1 H NMR (400 MHz, CDCl 3 ):  = 7.71-7.58 (m,3 H),7.52 (d,J = 7.8 Hz,2 H),8 H),5 H),3 H),4.09 (d,J = 14.7 Hz,1 H),3.93 (d,J = 14.8 Hz, 1 H), 2.37 (s, 3 H), 1.76 (s, 3 H), 1.52 (s, 3 H). 13 C NMR (100 MHz, CDCl 3 ):  = 168.…”

Section: Hrms (Esimentioning

confidence: 99%

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Cinchona Alkaloid Catalyzed Dynamic Kinetic Resolution of Biaryl Aldehydes via Asymmetric Decarboxylative Transamination

Guo

Wang

2022

Synthesis

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The unprecedented Cinchona alkaloid catalyzed atropoenantioselective transamination of biaryl aldehydes with 2,2-diphenylglycine via a cascade decarboxylation and dynamic kinetic resolution strategy is described. This protocol features broad substrate scope and good functional group tolerance and allows the rapid assembly of axially chiral biaryls in high yields with acceptable to good enantioselectivities. In addition, such structural motifs may have potential applications in enantioselective catalysis as chiral ligands or catalysts.

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Section: Hrms (Esimentioning

confidence: 99%

“…7.08 (d, J = 7.3 Hz, 1 H), 7.02 (d, J = 5.2 Hz, 2 H), 6.88-6.75 (m,2 H),6.69 (d,J = 7.9 Hz,2 H),6.40 (d,J = 8.5 Hz,1 H),4.33 (d,J = 14.2 Hz, 1 H), 4.11 (d,J = 14.1 Hz,1 H),2.22 (s,3 H). 13 C NMR (100 MHz, CDCl 3 ):  = 169.0, 142.…”

Section: Guo Et Almentioning

confidence: 99%

Cinchona Alkaloid Catalyzed Dynamic Kinetic Resolution of Biaryl Aldehydes via Asymmetric Decarboxylative Transamination

Guo

Wang

2022

Synthesis

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“…Mimicking the biological process 14 , i.e., asymmetric biomimetic transamination, affords a highly intriguing method to synthesize NH 2 -free amines from readily available carbonyl compounds 15 – 17 . The chemistry has attracted much attention since the 1970s 18 – 36 . The studies mainly include stoichiometric chiral pyridoxamine-promoted asymmetric transamination of α-keto acids 18 – 21 , pyridoxal/pyridoxamine-catalyzed asymmetric transamination of α-keto acids 22 – 26 , and chiral base/Lewis acid-catalyzed asymmetric transamination of α-keto esters and activated ketones 27 – 36 .…”

Section: Introductionmentioning

confidence: 99%

“…The chemistry has attracted much attention since the 1970s 18 – 36 . The studies mainly include stoichiometric chiral pyridoxamine-promoted asymmetric transamination of α-keto acids 18 – 21 , pyridoxal/pyridoxamine-catalyzed asymmetric transamination of α-keto acids 22 – 26 , and chiral base/Lewis acid-catalyzed asymmetric transamination of α-keto esters and activated ketones 27 – 36 . Asymmetric transamination of α-keto amides can potentially provide an appealing new strategy to produce peptides.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric biomimetic transamination of α-keto amides to peptides

et al. 2021

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Peptides are important compounds with broad applications in many areas. Asymmetric transamination of α-keto amides can provide an efficient strategy to synthesize peptides, however, the process has not been well developed yet and still remains a great challenge in both enzymatic and catalytic chemistry. For biological transamination, the high activity is attributed to manifold structural and electronic factors of transaminases. Based on the concept of multiple imitation of transaminases, here we report N-quaternized axially chiral pyridoxamines 1 for enantioselective transamination of α-keto amides, to produce various peptides in good yields with excellent enantio- and diastereoselectivities. The reaction is especially attractive for the synthesis of peptides made of unnatural amino acids since it doesn’t need great efforts to make chiral unnatural amino acids before amide bond formation.

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“…In this context, several representative organocatalysts present two or more functional groups that act in cooperative or bifunctional strategies [12][13][14][15][16][17][18]. Several research groups have used natural and unnatural amino acids and peptides [19][20][21][22][23][24][25][26][27][28][29][30][31], chiral ureas and thioureas [32][33][34][35][36][37][38][39][40], and chiral amides [41][42][43][44][45] as building blocks or templates in organocatalyst design. In this context, a significant number of (S)-proline derivatives have been developed while searching for an improvement in the catalytic efficiency and stereoselectivity [46][47][48][49][50][51][52][53].…”

Section: Introductionmentioning

confidence: 99%

New Mesoporous Silica-Supported Organocatalysts Based on (2S)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol Reaction

et al. 2020

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Novel organocatalytic systems based on the recently developed (S)-proline derivative (2S)-[5-(benzylthio)-4-phenyl-(1,2,4-triazol)-3-yl]-pyrrolidine supported on mesoporous silica were prepared and their efficiency was assessed in the asymmetric aldol reaction. These materials were fully characterized by FT-IR, MS, XRD, and SEM microscopy, gathering relevant information regarding composition, morphology, and organocatalyst distribution in the doped silica. Careful optimization of the reaction conditions required for their application as catalysts in asymmetric aldol reactions between ketones and aldehydes afforded the anticipated aldol products with excellent yields and moderate diastereo- and enantioselectivities. The recommended experimental protocol is simple, fast, and efficient providing the enantioenriched aldol product, usually without the need of a special work-up or purification protocol. This approach constitutes a remarkable improvement in the field of heterogeneous (S)-proline-based organocatalysis; in particular, the solid-phase silica-bonded catalytic systems described herein allow for a substantial reduction in solvent usage. Furthermore, the supported system described here can be recovered, reactivated, and reused several times with limited loss in catalytic efficiency relative to freshly synthesized organocatalysts.

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Asymmetric Synthesis of α-Amino Acids by Organocatalytic Biomimetic Transamination

Cited by 16 publications

References 35 publications

Cinchona Alkaloid Catalyzed Dynamic Kinetic Resolution of Biaryl Aldehydes via Asymmetric Decarboxylative Transamination

Cinchona Alkaloid Catalyzed Dynamic Kinetic Resolution of Biaryl Aldehydes via Asymmetric Decarboxylative Transamination

Asymmetric biomimetic transamination of α-keto amides to peptides

New Mesoporous Silica-Supported Organocatalysts Based on (2S)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol Reaction

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