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Synlett 1993; 1993(12): 921-923
DOI: 10.1055/s-1993-22653
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Convenient Preparation of Stereochemically Homogeneous 2-Acyl-3-sulfonyl-1,3-oxazolidines and Diastereoselective Grignard Additions to Form Protected Enantiopure 2-Hydroxyalkanals1

Kilian Conde Frieboes* , Timm Harder, Dirk Aulbert, Cordula Strahringer, Michael Bolte, Dieter Hoppe
  • *Institut für Organische Chemie, Universität Frankfurt, Niederurseler Hang, D-60439 Frankfurt, Germany
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Publication History

Publication Date:
19 March 2002 (online)

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Enantiomerically pure, protected 2-hydroxyalkanals are obtained by highly diastereoselective addition of Grignard reagents onto 2-acyl-3-arenesulfonyl-1,3-oxazolidines. The ketones are readily prepared from the appropriate 2-methoxy-1,3-oxazolidines via the 2-cyano derivatives again by Grignard addition. Several options are offered in order to direct the configuration of the newly formed stereocenter.