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Synthesis 1999; 1999(2): 237-242
DOI: 10.1055/s-1999-3397
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Asymmetric Michael Additions via 6- and 7-Membered Lactone SAMP-Hydrazones: Diastereo- and Enantioselective Synthesis of Substituted Lactone Esters

Dieter Enders* , Pascal Teschner, Robert Gröbner, Gerhard Raabe
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-52074 Aachen, Germany; Fax +49(2 41)8 88 81 27; E-mail: Enders@RWTH-Aachen.de
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Publikationsdatum:
31. Dezember 1999 (online)

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Lactone esters (S/R,S)-5a-f were synthesized in good overall yields (37-61%, two steps) and diastereo- and enantiomeric excesses (de = 88-≥96%, ee = 81 -≥96%) by 1,4-addition of metalated lactone-SAMP-hydrazones (S)-2 to enoate Michael acceptors 3 and subsequent oxidative cleavage of the product hydrazones by ozonolysis. The relative and absolute configuration was determined by X-ray structure analysis of (R,S)-5c.

asymmetric synthesis - Michael addition - lactone hydrazones - lactone esters - SAMP/RAMP hydrazone method

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