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Synthesis 1991; 1991(6): 465-469
DOI: 10.1055/s-1991-26495
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Inversion of Configuration of Alcohols with O-Alkyl-N,N′-dicyclohexylisoureas

Rolf Jaeger*
  • *Institut für Organische Chemie der Universität Kiel, Olshausenstr. 40-60, D-2300 Kiel 1, Germany
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Publication Date:
29 April 2002 (online)

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(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)phenols [(S)- 5] and [(S)-6], respectively, are formed simultaneously. These byproducts, besides others resulting from hydride-shifts, document that the mechanism proceeds via the methylheptyl cation intermediate.