203314-91-4Relevant academic research and scientific papers
Diastereo- and enantioselective synthesis of syn-2,3-disubstituted 1,4-diketones via oxidative coupling of metalated hydrazones
Enders, Dieter,Müller, Peter,Klein, Daniela
, p. 43 - 44 (1998)
An efficient diastereo- and enantioselective synthesis of syn-2,3-disubstituted 1,4-diketones 4 is described. Key step of the procedure is the oxidative coupling of the metalated SAMP/RAMP-hydrazones 2 with iodine, followed by oxidative cleavage of the dimerized bishydrazones 3 with ozone and subsequent separation of the minor meso-isomer by chromatography. The d,l-isomers of the title 1,4-diketones 4 are obtained in good overall yields (20-64%) and high diastereo- and enantiomeric excesses (de ≥ 98%, ee = 80 - ≥95%).
