Organic Letters
Letter
Structural Characterization of a Novel Selective Androgen Receptor
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(9) Biltz, H. Uber die Konstitution der Einwirkungsprodukte von
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(23) Crystal structure of 8k is available at CCDC under number
1869712.
(24) (a) Sallam, A. A.; Mohyeldin, M. M.; Foudah, A. I.; Akl, M. R.;
Nazzal, S.; Meyer, S. A.; Liu, Y. Y.; El Sayed, K. A. Marine Natural
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(25) Only a trace amount of nitrile resulting from decarboxylative
cyanation of peptide 11a was isolated and characterized by HRMS
after 48 h at 50 °C. A SET pathway for hydantoin synthesis would be
expected to lead to a higher extent of such a side product.
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(11) Urech, F. Ueber Lacturaminsaure und Lactylharnstoff. Justus
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(12) It is unclear in the following publications if the hydantoins
obtained are optically pure when using chiral aminoesters and amino
amide, respectively. (a) Bogolubsky, A. V.; Moroz, Y. S.; Savych, O.;
Pipko, S.; Konovets, A.; Platonov, M.; Vasylchenko, O. V.; Hurmach,
V. V.; Grygorenko, O. O. An Old Story in the Parallel Synthesis
World: An Approach to Hydantoin Libraries. ACS Comb. Sci. 2018,
20, 35. (b) Dumbris, S. M.; Diaz, D. J.; McElwee-White, L.
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(13) Zhang, D.; Xing, X.; Cuny, G. D. Synthesis of Hydantoins from
Enantiomerically Pure α-Amino Amides without Epimerization. J.
Org. Chem. 2006, 71, 1750.
(14) Liu, H.; Yang, Z.; Pan, Z. Synthesis of Highly Substituted
Imidazolidine-2,4-dione (Hydantoin) through Tf2O-Mediated Dual
Activation of Boc-Protected Dipeptidyl Compounds. Org. Lett. 2014,
16, 5902.
(15) Chen, Y.; Su, L.; Yang, X.; Pan, W.; Fang, H. Enantioselective
Synthesis of 3,5-Disubstituted Thiohydantoins and Hydantoins.
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(16) Tanwar, D. K.; Ratan, A.; Gill, M. S. Facile One-Pot Synthesis
of Substituted Hydantoins from Carbamates. Synlett 2017, 28, 2285.
(17) Song, J.; Zhang, Z.-J.; Chen, S.-S.; Fan, T.; Gong, L.-Z. Lewis
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(18) (a) Le Vaillant, F.; Courant, T.; Waser, J. Room-Temperature
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(21) (a) Wang, Y. F.; Qiu, J.; Kong, D.; Gao, Y.; Lu, F.; Karmaker, P.
G.; Chen, F. X. The Direct Electrophilic Cyanation of β-Keto Esters
and Amides With Cyano Benziodoxole. Org. Biomol. Chem. 2015, 13,
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Org. Lett. XXXX, XXX, XXX−XXX