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Synthesis 1994; 1994(1): 66-72
DOI: 10.1055/s-1994-25407
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(S,S)-3,5-Dimethylmorpholine, a Novel C 2-Symmetric Auxiliary. First Application in [4+2]-Cycloadditions Leading to 4-Oxohexahydropyridazine Derivatives

Dieter Enders* , Oliver Meyer, Gerhard Raabe, Jan Runsink
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-52074 Aachen, Germany
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Publication Date:
17 September 2002 (online)

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Diastereoselective Diels-Alder reactions of (S,S)-2-(3,5-dimethylmorpholino) butadienes 10 with aza-dienophiles are described, leading to cycloadducts 12 in good yields and high stereoselectivities (de = 87-96%). After double bond migration to 13, acidic and basic hydrolysis affords 4-oxohexahydropyridazine derivatives 14 and 16 of high enantiomeric purity (ee = 90-91%). The configuration of the new stereogenic centre is determined by NOE-measurements and an X-ray structure analysis of the cycloadduct (R,S,S)- 13f.