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Synlett 2000; 2000(3): 388-390
DOI: 10.1055/s-2000-6543
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High Stereochemical Fidelity in Reactions of an Atropisomeric N-Acyliminium Intermediate

Christopher R. A. Godfrey* , Nigel S. Simpkins, Matthew D. Walker
  • *Zeneca Agrochemicals, Jealott's Hill Research Station, Bracknell, Berkshire RG42 6ET, UK; Fax +44 1 15 9 51 35 64; E-mail: nigel.simpkins@nottingham.ac.uk
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Publication History

Publication Date:
31 December 2000 (online)

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Atropisomeric lactams bearing a chiral auxiliary were prepared by condensation of l-menthol with N-ortho-tert-butylphenyl-5-hydroxypyrrolidin-2-one. Substitution reactions of these compounds, via N-acyliminium intermediates, were demonstrated to be controlled by the C-N axis with a high degree of fidelity.

allylations - atropisomerism - chiral auxiliaries - lactams - N-acyliminium