Enantio- and Diastereoselective Synthesis of (Protected) 2-Formyl- and 2-(Hydroxymethyl)-1-phenylalkane-1,3-diols from Chiral 2-Methoxy-3-tosyl-1,3-oxazolidines by Subsequent Asymmetric Formylation and Aldolization

Frank Steif; Birgit Wibbeling; Oliver Meyer; Dieter Hoppe

doi:10.1055/s-2000-6393

Synthesis 2000; 2000(5): 743-753
DOI: 10.1055/s-2000-6393

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Enantio- and Diastereoselective Synthesis of (Protected) 2-Formyl- and 2-(Hydroxymethyl)-1-phenylalkane-1,3-diols from Chiral 2-Methoxy-3-tosyl-1,3-oxazolidines by Subsequent Asymmetric Formylation and Aldolization

Frank Steif^* , Birgit Wibbeling, Oliver Meyer, Dieter Hoppe

^*Institut für Organische Chemie der Westfälischen Wilhelms-Universität Münster, Corrensstraße 40, D-48149 Münster, Germany; Fax + 49(251)8 33 97 72

Abstract

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Trimethylsilyl enol ethers are successively converted into chirally protected α-formyl ketones by asymmetric formylation with the 2-methoxy-1,3-oxazolidine 2, transformed into the corresponding, thermodynamically determined (Z)-TMS enol ethers, and then are allowed to condense with aldehydes. All steps proceed with high stereoselectivity. Some synthetic options, arising from the three differentiated oxygen functionalities in the intermediates 8 are illustrated for the title target compounds.

chiral 3-arensulfonyl-1,3-oxazolidines - asymmetric formylation - diastereoselective aldolization - titanium enolates - chiral alkane-1,3-diols - ketones - chiral auxiliaries

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