Synthesis

Inversion of Configuration of Alcohols with O-Alkyl-N, N′-dicyclohexylisoureas

R Jaeger

Index: Jaeger Synthesis, 1991 , # 6 p. 465 - 469

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Citation Number: 6

Abstract

(S)-(+)-N, N'-Dicyclohexyl-O-(1-methylheptyl) isourea [(S)-2] reacts with acetic acid in cyclohexane to give (R)-(—)-(1-methylheptyl) acetate [(R)-3] with 100% inversion of configuration. Reaction of isourea (R)-2 with phenol proceeds also with inversion of configuration (99.8%) yielding (S)-(+)-(1-methylheptyl) phenyl ether [(S)-4] as the main product; optically active 2-and 4-(1-methylheptyl) phcnols [(S)-5] and [(S)-6], respectively, ...