Synthesis of Dihydroxyethylene Isosteres of Dipeptides. 1. Enantiomerically and Diastereomerically Pure 2-Alkyl-5-amino-3-dimethylphenylsilyl-4-octanolides from (S)-N,N-Dibenzylleucinal

Frank Rehders; Dieter Hoppe

doi:10.1055/s-1992-26247

Synthesis 1992; 1992(9): 859-864
DOI: 10.1055/s-1992-26247

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Synthesis of Dihydroxyethylene Isosteres of Dipeptides. 1. Enantiomerically and Diastereomerically Pure 2-Alkyl-5-amino-3-dimethylphenylsilyl-4-octanolides from (S)-N,N-Dibenzylleucinal

Frank Rehders^* , Dieter Hoppe

^*Institut für Organische Chemie der Universität Kiel, Olshausenstr. 40, D-2300 Kiel 1, Germany

Abstract

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5-Dibenzylamino-3-dimethylphenylsilyl-4-octanolides are prepared via homoenolate addition of (S)-N,N-dibenzylleucinal [(S)-2-dibenzylamino-4-methylpentanal] and metalated 3-dimethylphenylsilyl-2-propenyl N,N-diisopropylcarbamate, followed by oxidative lactonization. Subsequently, alkyl groups are introduced stereoselectively to the 2-position by means of enolate methodology to yield the title compounds, which are valuable intermediates in the synthesis of dipeptide isosteres.

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