Synthesis of New Chiral and Racemic 1,3‐Dioxolanes

Abstract

A series of chiral 1,3-dioxolanes, 3-12, with >99% ee values, have been synthesized. This is the first study of chiral ketalization reaction starting from ketones with aryl, monosubstituted aryl, and long alkyl chains (C 11 -AC 13 ). Their ee values were determined by chiral high-performance liquid chromatography (HPLC) on Chiralcel OD column, using their racemic 1,3-dioxolanes rac-3-12, which were also synthesized for the first time. These chiral and racemic 1,3-dioxolanes were characterizated by infrared, NMR ( 1 H, 13 C), mass spectrometry, elemental analysis, optical rotation, and chiral HPLC.

Synthesis and Biological Activity of New 1,3-Dioxolanes as Potential Antibacterial and Antifungal Compounds

“…K10 was investigated, however these reactions required long reaction times because the diols used in this study were sterically hindered. In our previous study [16], ketones with long alkyl chain were activated by trimethyl orthoformate (TMOF) to react with diols successfully in good yields and high enantiomeric excesses (>99% ee). In the literature [22,23,24], TMOF has been added in only a few studies as additive.…”

“…In the literature [22,23,24], TMOF has been added in only a few studies as additive. Based on the previous study [16], salicylaldehyde was converted via TMOF to its more reactive dimethyl acetal (Scheme 1). This acetal participated then successfully in the acetalization reactions with chiral (compounds a,b,d,e,g) and racemic diols (compounds c,f,h) with shorter reaction times, good yields and high enantiomeric excesses (>99% ee).…”

“…2,2'-bis(Hydroxymethyl) norborn-5-ene and ethylene glycol were used as 1,2-diol functionalities. We have recently reported [16] the synthesis of chiral and racemic 1,3-dioxolanes with aryl, mono substituted aryl and long alkyl chain groups (C 11 -C 13 ).…”