Synthesis and structure of 2-aryl-5, 5-disubstituted-1, 3-dioxanes and conversion into chiral (1, 1, 1-trishydroxymethyl) methane derivatives

Abstract

Pentaerythritol, (1,1,1-trishydroxymethyl)methyl methane and (1,1,1-trishydroxymethyl)nitromethane are converted into 2-aryl-5,5-bis(hydroxymethyl), 2-aryl-5-hydroxymethyl-5-methyl- or 2-aryl-5-hydroxymethyl-5-nitro-1,3-dioxanes and a range of derivatives. X-Ray and NMR analysis establishes that the latter is obtained as a single diastereomer whose structure is unambiguously determined. These materials can be elaborated to chiral derivatives of the starting (1,1,1-trishydroxymethyl) methanes.