- SYNTHESIS OF ENANTIOMERICALLY PURE (5S)-4-AZA-2-OXA-6,6-DIMETHYL-7,10-METHYLENE-5-SPIRODECAN-3-ONE, A NOVEL CHIRAL OXAZOLIDIN-2-ONE FROM (-)-CAMPHENE FOR USE AS A RECYCLABLE CHIRAL AUXILIARY IN ASYMMETRIC TRANSFORMATIONS
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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.
- Banks, Malcolm R.,Cadogan, J. I. G.,Gosney, Ian,Grant, Keith J.,Hodgson, Philip K. G.,Thorburn, Paul
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p. 199 - 206
(2007/10/02)
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- Exploiting Steric Shielding : Tuning Terpenoid-Derived Oxazolidin-2-ones as Chiral Auxiliarites for the Diels-Alder Reaction
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Preparative metodology is described for acces to three different terpenoid-derived oxazolidin-2-ones 4,8,and 11, of which the latter, obtained from camphene in four steps, provides virtualy complete asymmetric induction when acting as a chiral auxilarity in Diels-Alder cycloaddition reactions with cyclopentadiene.
- Banks, Malcolm R.,Blake, Alexander J.,Brown, Angus R.,Cadogan, J. I. G.,Gaur, Suneel,et al.
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p. 489 - 492
(2007/10/02)
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