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Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Perspective

The Intra- and Intermolecular Friedel-Crafts Acylation of Amino Acid Derivatives in Stereo-retarded Manner

Author(s): Zetryana Puteri Tachrim* and Makoto Hashimoto*

Volume 28, Issue 16, 2024

Published on: 14 May, 2024

Page: [1225 - 1228] Pages: 4

DOI: 10.2174/0113852728317263240510114622

Price: $65

Abstract

The Friedel-Crafts acylation of natural or unnatural amino acids in stereoretarded manner is willing to prescribed here. Depending on its main skeleton, the typical intra- and intermolecular Friedel-Crafts reaction of amino acids can be differentiated. The unique amino acid’s general structure can contribute to the reaction between its carboxyl group and the side chain. Depending on the Friedel-Crafts reaction condition, the amino acid’s optical retention can be retarded. This perspective can contribute to the development of this one-century reaction in the field of organic chemistry.

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Graphical Abstract

[1]
Sumita, A.; Ohwada, T. Friedel-crafts-type acylation and amidation reactions in strong brønsted acid: Taming superelectrophiles. Molecules, 2022, 27(18), 5984.
[http://dx.doi.org/10.3390/molecules27185984] [PMID: 36144714]
[2]
Concellon, J.; Rodriguez-Solla, H. Synthesis and synthetic applications of α-amino ketones derived from natural α-amino acids. Curr. Org. Chem., 2008, 12(7), 524-543.
[http://dx.doi.org/10.2174/138527208784245996]
[3]
Wang, L.; Murai, Y.; Yoshida, T.; Okamoto, M.; Tachrim, Z.; 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.
[http://dx.doi.org/10.3390/molecules19056349] [PMID: 24840903]
[4]
Itoh, O.; Honnami, T.; Amano, A.; Murata, K.; Koichi, Y.; Sugita, T. Friedel-crafts. alpha.-aminoacylation of alkylbenzene with a chiral N-carboxy-.alpha.-amino acid anhydride without loss of chirality. J. Org. Chem., 1992, 57(26), 7334-7338.
[http://dx.doi.org/10.1021/jo00052a059]
[5]
Angelaud, R.; Zhong, Y.L.; Maligres, P.; Lee, J.; Askin, D. Synthesis of a β-amino acid pharmacophore via a β-lactam intermediate. J. Org. Chem., 2005, 70(5), 1949-1952.
[http://dx.doi.org/10.1021/jo048249c] [PMID: 15730331]
[6]
Griesbeck, A.; Heckroth, H. A simple approach to β-amino acids by acylation of arenes with N-acyl aspartic anhydrides. Synlett, 1997, 1997(11), 1243-1244.
[http://dx.doi.org/10.1055/s-1997-1007]
[7]
Mi, A.; Lin, W.; He, Z.; Zhang, H.; Zhang, X.; Jiang, Y. Amino acid anhydride hydrochlorides as acylating agents in Friedel-crafts reaction: A practical synthesis of l-homophenylalanine. Synthesis, 2001, 2001(7), 1007-1009.
[http://dx.doi.org/10.1055/s-2001-14563]
[8]
Xu, Q.; Wang, G.; Wang, X.; Wu, T.; Pan, X.; Chan, A.S.C.; Yang, T.K. The synthesis of L-. homophenylalanine hydrochloride. Tetrahedron Asymmetry, 2000, 11(11), 2309-2314.
[http://dx.doi.org/10.1016/S0957-4166(00)00193-2]
[9]
Murashige, R.; Hayashi, Y.; Hashimoto, M. Asymmetric and efficient synthesis of homophenylalanine derivatives via Friedel-crafts reaction with trifluoromethanesulfonic acid. Tetrahedron Lett., 2008, 49(46), 6566-6568.
[http://dx.doi.org/10.1016/j.tetlet.2008.09.013]
[10]
Seki, M.; Kubota, H.; Moriya, T.; Yamagishi, M.; Nishimoto, S.; Matsumoto, K. Useful syntheses of. BETA.-amino-.GAMMA.-ketobutyric acid derivatives from aspartic acid. Chem. Pharm. Bull. (Tokyo), 1986, 34(11), 4516-4522.
[http://dx.doi.org/10.1248/cpb.34.4516]
[11]
Apostol, T.V.; Chifiriuc, M.C.; Socea, L.I.; Draghici, C.; Olaru, O.T.; Nitulescu, G.M.; Visan, D.C.; Marutescu, L.G.; Pahontu, E.M.; Saramet, G.; Barbuceanu, S.F. Synthesis, characterization, and biological evaluation of novel N-4-[(4-bromophenyl)sulfonyl]benzoyl-L-valine derivatives. Processes, 2022, 10(9), 1800.
[http://dx.doi.org/10.3390/pr10091800]
[12]
Nordlander, J.E.; Payne, M.J.; Njoroge, F.G.; Balk, M.A.; Laikos, G.D.; Vishwanath, V.M. Friedel-Crafts acylation with N-(trifluoroacetyl)-.α.-amino acid chlorides. Application to the preparation of. β.-arylalkylamines and 3-substituted 1,2,3,4-tetrahydroisoquinolines. J. Org. Chem., 1984, 49(22), 4107-4111.
[http://dx.doi.org/10.1021/jo00196a001]
[13]
Tachrim, Z.; Wang, L.; Murai, Y.; Yoshida, T.; Kurokawa, N.; Ohashi, F.; Hashidoko, Y.; Hashimoto, M. Trifluoromethanesulfonic acid as acylation catalyst: special feature for C- and/or O-acylation reactions. Catalysts, 2017, 7(12), 40-68.
[http://dx.doi.org/10.3390/catal7020040]
[14]
Katritzky, A.R.; Jiang, R.; Suzuki, K. N-Tfa- and N-Fmoc-(α-aminoacyl)benzotriazoles as chiral C-acylating reagents under Friedel-crafts reaction conditions. J. Org. Chem., 2005, 70(13), 4993-5000.
[http://dx.doi.org/10.1021/jo050226q] [PMID: 15960497]
[15]
Katritzky, A.R.; Tao, H.; Jiang, R.; Suzuki, K.; Kirichenko, K. Novel syntheses of chiral β- and γ-amino acid derivatives utilizing N-protected (aminoacyl)benzotriazoles from aspartic and glutamic acids. J. Org. Chem., 2007, 72(2), 407-414.
[http://dx.doi.org/10.1021/jo061667s] [PMID: 17221955]
[16]
Itoh, O.; Amano, A. Friedel-crafts α-aminoacylation of aromatic compounds with a chiral N-Carboxy-α-amino acid anhydride (NCA); Part 2. Synthesis, 1999, 1999(3), 423-428.
[http://dx.doi.org/10.1055/s-1999-3405]
[17]
Effenberger, F.; Steegmüller, D.; Null, V.; Ziegler, T. Intramolekulare Friedel‐crafts‐acylierung von N‐phthaloyl‐substitutierten Aryl‐ und homophenylalanylchloriden. Chem. Ber., 1988, 121(1), 125-130.
[http://dx.doi.org/10.1002/cber.19881210119]
[18]
Zhao, R.; Guo, P.; Dong, J.; Zhang, X.; Sun, X.; Tian, Y.; Zeng, Q. Synthesis of 2-amino-1-indanone from DL-phenylalanine. Org. Prep. Proced. Int., 2011, 43(4), 377-380.
[http://dx.doi.org/10.1080/00304948.2011.582014]
[19]
Hashimoto, M.; Puteri Tachrim, Z.; Oida, K.; Ohashi, F.; Wakasa, H.; Ikemoto, H.; Kurokawa, N.; Sakihama, Y.; Hashidoko, Y.; Suzuki, T. TFA-] protected α-amino acid n-hydroxysuccinimide ester: Application for inter-] and intramolecular acylation. Heterocycles, 2018, 97(2), 877-893.
[http://dx.doi.org/10.3987/COM-18-S(T)65]
[20]
Murai, Y.; Wang, L.; Masuda, K.; Sakihama, Y.; Hashidoko, Y.; Hatanaka, Y.; Hashimoto, M. Rapid and controllable hydrogen/deuterium exchange on aromatic rings of α -amino acids and peptides. Eur JOC, 2013, 2013(23), 5111-5116.
[http://dx.doi.org/10.1002/ejoc.201300405]
[21]
Abdolmaleki, A.; Mallakpour, S.; Borandeh, S. Structure, morphology and electronic properties of L-phenylalanine edge-functionalized graphite platelets through Friedel-crafts acylation reaction. RSC Advances, 2014, 4(104), 60052-60057.
[http://dx.doi.org/10.1039/C4RA10387D]
[22]
Nikam, S.B. S K, A. Enantioselective separation of amino acids using chiral polystyrene microspheres synthesized by a post-polymer modification approach. ACS Polym. Au, 2022, 2(4), 257-265.
[http://dx.doi.org/10.1021/acspolymersau.2c00004] [PMID: 36855562]

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