3578-33-4Relevant academic research and scientific papers
The double addition reaction of alkoxymethyl nucleophiles to esters to generate novel polyoxygenated species
Verma, Vishal A.,Arasappan, Ashok,Njoroge, F. George
experimental part, p. 4284 - 4286 (2010/09/07)
The development of a double addition reaction of alkoxylmethyl nucleophiles to a variety of functionalized aryl and alkyl esters to give polyoxygenated products is reported. Key features include broad electrophile substrate scope and good yields. Structurally diverse nucleophiles were investigated and were found to successfully undergo diaddition. This development now allows facile access to this novel class of polyoxygenated molecules.
Enantioselective Syntheses of 2-Deoxyxylono-1,4-lactone and 2-Deoxyribono-1,4-lactone from 1,3-Dioxan-5-yl Diazoacetates
Doyle, Michael P.,Tedrow, Jason S.,Dyatkin, Alexey B.,Spaans, Coenraad J.,Ene, Doina G.
, p. 8907 - 8915 (2007/10/03)
1,3-Dioxan-5-yl diazoacetates are valuable substrates for highly diastereoselective and enantio-selective carbon-hydrogen insertion reactions. trans-2-(tert-Butyl)-1,3-dioxan-5-yl diazoacetate is a direct precursor to 2-deoxyribono-1,4-lactone in up to 81% ee, whereas cis-2-(tert-butyl)-1,3-dioxan-5-yl diazoacetate yields only the protected 2-deoxyxylono-1,4-lactone in up to 96% ee. However, trans-2-aryl-1,3-dioxan-5-yl diazoacetate (aryl = phenyl or 2-naphthyl) forms the precursor to 2-deoxyxylono-1,4-lactone in up to 95% ee but with the mirror image configuration of that produced from the trans-2-(tert-butyl) analogue. The catalysts that are most suitable for these carbon-hydrogen insertion reactions are chiral dirhodium(II) carboxamidates. 1,3-Dialkoxy-2-propyl diazoacetates give mainly 2-deoxyxylono-1,4-lactone derivatives (>90:10) with generally high enantiocontrol, but replacement of hydrogen at the 2-position of these 2-propyl diazoacetates led to a mixture of products.
