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Synlett 1998; 1998(1): 43-44
DOI: 10.1055/s-1998-1562
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Diastereo- and Enantioselective Synthesis of syn-2,3-Disubstituted 1,4-Diketones via Oxidative Coupling of Metalated Hydrazones

Dieter Enders* , Peter Müller, Daniela Klein
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, 52074 Aachen, Germany; Fax (int.) +2 41 88 88 1 27; E-mail: Enders@RWTH-Aachen.de
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Publication History

Publication Date:
31 December 2000 (online)

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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%).

1,4-diketones - asymmetric synthesis - oxidative coupling - SAMP/RAMP hydrazone method

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