Selective reductions of 3-substituted hydantoins to 4-hydroxy-2-imidazolidinones and vicinal diamines

S Cortes, H Kohn

Index: Cortes, Sergio; Kohn, Harold Journal of Organic Chemistry, 1983 , vol. 48, # 13 p. 2246 - 2254

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Citation Number: 33

Abstract

N3-Substituted hydantoins (1) have been shown to undergo LM 4 reduction (THF, room temperature, 2 days) to give 4-hydroxy-2-imidazolidinones (3) in good yields. Reduction of 3, Ci-disubstituted hydantoins in which an aliphatic substituent was present at nitrogen 3 led to the preferential formation of the cis adduct 3. Conversely, disubstituted hydantoins possessing an aryl moiety at nitrogen 3 gave the trans derivative 3 as the major product. ...