DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF SYN-2,3-DISUBSTITUTED 1,4-DIKETONES VIA OXIDATIVE COUPLING OF METALATED HYDRAZONES

Authors
ENDERS D MULLER P KLEIN D
Citation
D. Enders et al., DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF SYN-2,3-DISUBSTITUTED 1,4-DIKETONES VIA OXIDATIVE COUPLING OF METALATED HYDRAZONES, Synlett, (1), 1998, pp. 43
Citations number
40
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
1
Year of publication
1998
Database
ISI
SICI code
0936-5214(1998):1<43:DAESOS>2.0.ZU;2-Y
Abstract
An efficient diastereo- and enantioselective synthesis of syn-2,3-disu bstituted 1,4-diketones 4 is described. Key step of the procedure is t he oxidative coupling of the metalated SAMP/RAMP-hydrazones 2 with iod ine, followed by oxidative cleavage of the dimerized bishydrazones 3 w ith ozone and subsequent separation of the minor meso-isomer by chroma tography. The d,l-isomers of the title 1,4-diketones 4 are obtained in good overall yields (20 - 64%) and high diastereo- and enantiomeric e xcesses (de greater than or equal to 98%, ee = 80 - greater than or eq ual to 95%).