336195-71-2Relevant academic research and scientific papers
Diastereoselective construction of anti-4,5-disubstituted-1,3-dioxolanes via a bismuth-mediated two-component hemiacetal oxa-conjugate addition of γ-hydroxy-α,β-unsaturated ketones with paraformaldehyde
Grisin, Aleksandr,Oliver, Samuel,Ganton, Michael D.,Bacsa, John,Evans, P. Andrew
supporting information, p. 15681 - 15684 (2015/11/02)
The bismuth-mediated two-component hemiacetal oxa-conjugate addition of γ-hydroxy-α,β-unsaturated ketones with paraformaldehyde affords anti-4,5-disubstituted-1,3-dioxolanes in an efficient and stereoselective manner. The reaction provides a practical, inexpensive and atom-economical approach to these types of heterocycles, which represent useful intermediates for target-directed synthesis and precursors to syn-1,2-diols.
Claisen-johnson orthoester rearrangement of γ-hydroxy α,β-unsaturated ketones and nitriles
Giardina, Alessandra,Marcantoni, Enrico,Mecozzi, Tiziana,Petrini, Marino
, p. 713 - 718 (2007/10/03)
Unsaturated γ-hydroxy ketones 3 and γ-hydroxy nitriles 7 are readily converted into 4-oxo esters 4 and 3-cyano esters 8 by means of a Claisen-Johnson orthoester rearrangement, using triethyl orthoacetate in xylene at reflux. The obtained ester derivatives can be selectively reduced at the carbonyl and cyano groups to afford the corresponding lactones 5 and pyrrolidinones 14.
