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Revisiting the Urech Synthesis of Hydantoins: Direct Access to Enantiopure 1,5-Substituted Hydantoins Using Cyanobenziodoxolone.

  • Declas N Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering , Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306 , 1015 Lausanne , Switzerland.
  • Le Vaillant F Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering , Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306 , 1015 Lausanne , Switzerland.
  • Waser J Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering , Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306 , 1015 Lausanne , Switzerland.
  • 2019-01-08
Published in:
  • Organic letters. - 2019
Physical and Theoretical Chemistry
Organic Chemistry
Biochemistry
English A method for the synthesis of enantiopure 1,5-substituted hydantoins was developed using a hypervalent iodine cyanation reagent (cyanobenziodoxolone, CBX) as a source of electrophilic carbon. Starting from inexpensive commercially available enantiopure protected amino acids, the method allowed the synthesis of various hydantoins without epimerization. Formation of hydantoins from dipeptides was also possible, but partial epimerization was observed in this case. This synthetic strategy is user friendly as CBX is a bench-stable easy-to-handle crystalline reagent and avoids conventional multistep protocols, thus allowing the facile synthesis of a library of chiral hydantoins.
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  • English
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green
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https://sonar.ch/global/documents/215015
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