Asymmetric Synthesis of Protected 2-Keto-1,3-diol and 1,2,3-Triol Building Blocks Bearing a Quaternary Stereogenic Center

Dieter Enders; Anja Nühring; Jan Runsink; Gerhard Raabe

doi:10.1055/s-2001-15236

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Asymmetric Synthesis of Protected 2-Keto-1,3-diol and 1,2,3-Triol Building Blocks Bearing a Quaternary Stereogenic Center

Dieter Enders*, Anja Nühring, Jan Runsink, Gerhard Raabe
Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, 52074 Aachen, Germany
Fax: +49(241)8888127; e-Mail: Enders@RWTH-Aachen.de;

Abstract

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Abstract

The asymmetric synthesis of protected 2-keto-1,3-diols 5 and 1,2,3-triols 6 bearing a quaternary stereogenic center starting from 2,2-dimethyl-1,3-dioxan-5-one (1) is described. The stereogenic centers are generated by sequential α-alkylation of 1 using the SAMP/RAMP hydrazone method and stereoselective reduction of ketones 5 with l-selectride. The products are obtained in good yields and high diastereomeric and enantiomeric excesses.

Keywords

2-keto-1,3-diols - 1,2,3-triols - asymmetric synthesis - quaternary stereogenic center - SAMP/RAMP hydrazones.

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References

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