Abstract
One-carbon homologation of carboxylic acids using diazomethane.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Arndt, F.; Eistert, B. Ber. 1935, 68, 200-208. Fritz Arndt (1885-1969) was born in Hamburg, Germany. He discovered the Arndt-Eistert homologation at the University of Breslau where he extensively investigated the synthesis of diazomethane and its reactions with aldehydes, ketones, and acid chlorides. Fritz Arndt’s chain-smoking of cigars ensured that his presence in the laboratories was always well advertised. Bernd Eistert (1902-1978), born in Ohlau, Silesia, was Arndt’s Ph.D. student. Eistert later joined I. G. Farbenindustrie, which became BASF after the Allies broke up the conglomerate following WWII.
Podlech, J.; Seebach, D. Angew. Chem. Int. Ed. 1995, 34, 471-472.
Matthews, J. L.; Braun, C.; Guibourdenche, C.; Overhand, M.; Seebach, D. In Enantioselective Synthesis of β-Amino Acids Juaristi, E. ed.; Wiley-VCH: Weinheim, Germany, 1996, pp 105-126. (Review).
Katritzky, A. R.; Zhang, S.; Fang, Y. Org. Lett. 2000, 2, 3789-3791.
Vasanthakumar, G.-R.; Babu, V. V. S. Synth. Commun. 2002, 32, 651-657.
Chakravarty, P. K.; Shih, T. L.; Colletti, S. L.; Ayer, M. B.; Snedden, C.; Kuo, H.; Tyagarajan, S.; Gregory, L.; Zakson-Aiken, M.; Shoop, W. L.; Schmatz, D. M.; Wyvratt, M. J.; Fisher, M. H.; Meinke, P. T. Bioorg. Med. Chem. Lett. 2003, 13, 147-150.
Gaucher, A.; Dutot, L.; Barbeau, O.; Hamchaoui, W.; Wakselman, M.; Mazaleyrat, J.-P. Tetrahedron: Asymmetry 2005, 16, 857-864.
Podlech, J. In Enantioselective Synthesis of β-Amino Acids (2nd Ed.) Wiley: Hoboken, NJ, 2005, pp 93-106. (Review).
Spengler, J.; Ruiz-Rodriguez, J.; Burger, K.; Albericio, F. Tetrahedron Lett. 2006, 47, 4557-4560.
Toyooka, N.; Kobayashi, S.; Zhou, D.; Tsuneki, H.; Wada, T.; Sakai, H.; Nemoto, H.; Sasaoka, T.; Garraffo, H. M.; Spande, T. F.; Daly, J. W. Bioorg. Med. Chem. Lett. 2007, 17, 5872-5875.
Fuchter, M. J. Arndt–Eistert Homologation. In Name Reactions for Homologations-Part I; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2009, pp 336-349. (Review).
Pinho, V. D.; Gutmann, B.; Kappe, C. O. RSC Adv. 2014, 4, 37419-37422.
Zarezin, D. P.; Shmatova, O. I.; Nenajdenko, V. G. Org. Biomol. Chem. 2018, 16, 5987-5998.
Castoldi, L.; Ielo, L.; Holzer, W.; Giester, G.; Roller, A.; Pace, V. J. Org. Chem. 2018, 83, 4336-4347.
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 2021 Springer Nature Switzerland AG
About this chapter
Cite this chapter
Li, J.J. (2021). Arndt–Eistert Homologation. In: Name Reactions. Springer, Cham. https://doi.org/10.1007/978-3-030-50865-4_3
Download citation
DOI: https://doi.org/10.1007/978-3-030-50865-4_3
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-50864-7
Online ISBN: 978-3-030-50865-4
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)