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Communication | Special issue | Vol 37, No. 1, 1994, pp.199-206
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S28
Synthesis of Enantiomerically Pure (5S)-4-Aza-2-oxa-6,6-dimethyl-7,10-methylene-5-spiro[4.5]-decan-3-one, a Novel Chiral Oxazolidin-2-one from (-)-Camphene for Use as a Recyclable Chiral Auxiliary in Asymmetric Transformations

Malcolm R. Banks, J. I. G. Cadogan, Ian Gosney,* Keith J. Grant, Philip K. G. Hodgson, and Paul Thorburn

*Department of Chemistry, The University of Edinburgh, King's Buildings, West Mains Road Edinburgh, EH9 3JJ, U.K.

Abstract

By an intramolecular nitreno-mediated route (-)-camphene is transformed into a novel spiro-oxazolidin-2-one whose efficiency as a chiral auxiliary is highlighted by the excellent levels of chiral induction attained in an array of asymmetric transformations such as the Diels -Alder, conjugate addition, aldol condensation, alkylation and acylation reactions.