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

doi:10.1055/s-1993-22653

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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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Publikationsdatum:
19. März 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.