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Synthesis 1994; 1994(12): 1313-1321
DOI: 10.1055/s-1994-25687
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Synthesis of Highly Functionalized, Enantiomerically and Diastereomerically Pure Cyclohexane Derivates via Michael Addition of Chiral 3-Tosyl-2-(2-oxoalkyl)-1,3-oxazolidines and Methyl Vinyl Ketone

Olaf Prien* , Holger Hoffmann, Kilian Conde-Frieboes, Thomas Krettek, Bernd Berger, Kerstin Wagner, Michael Bolte, Dieter Hoppe
  • *Institut für Organische Chemie der Universität Münster, Corrensstraße 40, D-48149 Münster, Germany
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Publication Date:
25 April 2002 (online)

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2-(2-Oxocycloalkyl)- or 2-phenylacyl-3-tosyl-1,3-oxazolidines 1, 2, 9, and 10 undergo with 3-buten-2-one highly diastereoselective Michael additions under the influence of cesium carbonate to yield 1,5-diketones 8 or 11, respectively. Intramolecular aldolization of diketones 8 yields stereohomogeneous cyclohexanones 13 or 14. Addition of nucleophiles to ketones 14, again, proceeds highly stereoselectively to give diols 17. Overall, under the stereodirecting influence of N-tosyl-2-aminoalkanols, stereohomogeneous protected carbaldehydes are constructed within a few steps from simple achiral precursors.

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