DOI: https://doi.org/10.55373/mjchem.v26i5.533

Keywords: Azido trimethylsilylcyclohexene; absolute configuration; vibrational circular dichorism (VCD); salen complex; Muricatacin

Abstract

A simple technique for absolute configuration determination of (1S,2S)-azido trimethylsilylcyclo-hexene 3 enantiomer is described. Samples were synthesized from racemic monoepoxide 1, via asymmetric epoxide ring opening catalyzed by (R,R)-salen complex, L-2 in the presence of trimethyl silylazide, TMSN3. (1S,2S)-azido trimethylsilylcyclohexene 3 and its corresponding racemic adduct were analyzed using VCD spectrometer. The VCD spectrums of boths compounds were recorded as linear regressions (dABS.) vs wavenumbers (cm-1). The major selected bands were analyzed to determine the absolute configuration of (1S,2S)-azido trimethylsilylcyclohexene 3. Compound 3 then underwent reduction and protection sequence to give 4. Allylic hydroxylation of 4 gave rise to compound 5 which was subjected to oxidative cleavage and lactonization steps that successfully afforded Muricatacin intermediate 6.