Utilization of Acidic α-Amino Acids as Acyl Donors: An Effective Stereo-Controllable Synthesis of Aryl-Keto α-Amino Acids and Their Derivatives
Abstract
:1. Introduction
2. General Methods to Prepare Aryl-keto α-Amino Acid Derivatives
2.1. α-Amino Acid Derivatives as the Reactants
2.2. Non-Amino Acid Derivatives as the Reactants
3. Preparation of Aryl Keto α-amino Acids by Friedel-Crafts Acylation
3.1. AlCl3 Catalyzed Friedel-Crafts Acylation
Substrate | arene | Time (h) | α/β-amino acids ratio | Yield (%) | Substrate | arene | Time (h) | α/β-amino acids ratio | Yield (%) |
---|---|---|---|---|---|---|---|---|---|
47a | benzene | 5 | 55/45 | 51 | 47c | toluene | 5 | 7/93 | 47 |
47a | toluene | 5 | 39/61 | 33 | 47c | o-xylene | 15 | 39/61 | 52 |
47a | o-xylene | 15 | 30/70 | 65 | 47d | benzene | 5 | 84/16 | 76 |
47a | mesitylene | 15 | 100/0 | 51 | 47d | toluene | 5 | 100/0 | 71 |
47a | anisole | 72 | 50/50 | 31 | 47d | o-xylene | 15 | 74/26 | 83 |
47a | veratrole | 96 | 100/0 | 18 | 47e | benzene | 5 | 95/5 | 78 |
47a | naphthalene | 15 | 95/5 | 44 | 47e | toluene | 5 | 80/20 | 62 |
47b | benzene | 5 | 95/5 | 76 | 47e | o-xylene | 15 | 56/44 | 70 |
47b | toluene | 5 | 64/36 | 52 | 37 | benzene | 5 | 100/0 | 64 |
47b | o-xylene | 15 | 58/42 | 67 | 37 | toluene | 5 | 88/12 | 71 |
47c | benzene | 5 | 30/70 | 55 | 37 | o-xylene | 15 | 48/52 | 83 |
3.2. HF Catalyzed Friedel-Crafts Acylation
3.3. TfOH Catalyzed Friedel-Crafts Acylation
Entry | Donor | Catalyst (eq) | Solvent | Reaction Time (h) | Product Yiled (%) |
---|---|---|---|---|---|
1 | 47e | AlCl3 (8) | CH2Cl2 | 1 or 12 | 0 |
2 | 47e | TiCl4 (90) | neat | 1 or 12 | 1 |
3 | 47e | H2SO4 (90) | neat | 1 or 12 | 2 |
4 | 47e | TfOH (40) | neat | 1 | 61a (52), 62 (3) |
5 | 47e | Tf2OH (25) | neat | 1 or 12 | 0 |
6 | 51 | TfOH (40) | neat | 1 | 0 |
7 | 60 | AlCl3 (8) | CH2Cl2 | 10 | 61b (50) |
8 | 60 | TiCl4 (90) | neat | 1 or 12 | 0 |
9 | 60 | H2SO4 (90) | neat | 1 or 12 | 0 |
10 | 60 | TfOH (40) | neat | 1 | 61b (98) |
11 | 60 | Tf2OH (25) | neat | 1 or 12 | 0 |
4. Conclusions
Acknowledgments
Conflicts of Interest
References
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Wang, L.; Murai, Y.; Yoshida, T.; Okamoto, M.; Tachrim, Z.P.; Hashidoko, Y.; Hashimoto, M. Utilization of Acidic α-Amino Acids as Acyl Donors: An Effective Stereo-Controllable Synthesis of Aryl-Keto α-Amino Acids and Their Derivatives. Molecules 2014, 19, 6349-6367. https://doi.org/10.3390/molecules19056349
Wang L, Murai Y, Yoshida T, Okamoto M, Tachrim ZP, Hashidoko Y, Hashimoto M. Utilization of Acidic α-Amino Acids as Acyl Donors: An Effective Stereo-Controllable Synthesis of Aryl-Keto α-Amino Acids and Their Derivatives. Molecules. 2014; 19(5):6349-6367. https://doi.org/10.3390/molecules19056349
Chicago/Turabian StyleWang, Lei, Yuta Murai, Takuma Yoshida, Masashi Okamoto, Zetryana Puteri Tachrim, Yasuyuki Hashidoko, and Makoto Hashimoto. 2014. "Utilization of Acidic α-Amino Acids as Acyl Donors: An Effective Stereo-Controllable Synthesis of Aryl-Keto α-Amino Acids and Their Derivatives" Molecules 19, no. 5: 6349-6367. https://doi.org/10.3390/molecules19056349