212518-21-3Relevant academic research and scientific papers
cis- and trans-2-(isocyanomethyl)-5,5-dimethyl-2-oxo-4-phenyl-1,3,2-dioxaphosphorinane - Synthesis and structure of the first chiral isocyanomethylphosphonate synthons
Weener, Jan-Willem,Versleijen, Jos P. G.,Meetsma, Auke,Ten Hoeve, Wolter,Van Leusen, Albert M.
, p. 1511 - 1516 (2007/10/03)
Both cis-2-(isocyanomethyl)-5,5-dimethyl-2-oxo-4-phenyl-1,3,2-dioxaphosphorinane (1a) and the trans epimer 1b have been prepared as potentially useful chiral isocyanomethylphosphonate synthons. 2-Methoxy-1,3,2-dioxaphosphorinanes 5 and the corresponding 2-ethoxy analog 6 were prepared from 2,2-dimethyl-1-phenyl-1,3-propanediol (2) and were converted in an Arbuzov-type reaction to 2-(formamidomethyl)oxo-1,3,2-dioxaphosphorinane 7, which upon dehydration gave 1a. Thus, both (±)-1a and (2S,4S)-(-)-1a were prepared, and their molecular structures were determined by single-crystal X-ray analysis. Treatment of (2S,4S)-(-)-1a with KF gave a 1:3 equilibrium mixture of the phosphorus epimers 1a and 1b, from which the predominant trans epimer (2S,4R)-(-)-1b was isolated by column chromatography and crystallisation.
