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Synthesis 1999; 1999(4): 635-638
DOI: 10.1055/s-1999-3428
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Alkylations of 2-Arylcyclohexyl Hippurates: Stereochemical Influence of π-electrons

John M. McIntosh* , Scott Peters
  • *Chemistry & Biochemistry, School of Physical Sciences, University of Windsor, Windsor, Ontario, Canada, N9B 3P4; Fax +1(5 19)9 73 70 98; E-mail: jmci@uwindsor.ca
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Publication Date:
31 December 1999 (online)

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The stereochemistry of alkylation of hippurate esters of trans 2-phenylcyclohexanol (1) and trans 2-(1-naphthyl)cyclohexanol (2) with a variety of electrophiles has been examined. Results with ester 1 indicate a small dependence of stereoselectivity on π-electron density. Ester 2 consistently gave diastereomeric ratios in excess of 90 : 10.

chiral hippurates - alkylation - π-electron systems