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Synthesis 1995; 1995(8): 947-951
DOI: 10.1055/s-1995-4431
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Enantioselective Synthesis of 2-Substituted 6- and 7-Membered Lactones via α-Alkylation of Lactone Hydrazones

Dieter Enders* , Robert Gröbner, Jan Runsink
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-52074 Aachen, Germany, Fax +49(241)8888127
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Publication Date:
31 December 2000 (online)

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2-Alkyl-substituted lactones 4 were synthesized in good overall yields and high enantiomeric purities (ee=90-94%) by deprotonation and alkylation of the corresponding lactone SAMP-hydrazones 2 and subsequent oxidative cleavage of the product hydrazones 3 by ozonolysis. The lactone hydrazones 2, in turn, were prepared in good yields by silver promoted cyclization of ω-chloroalkanohydrazides 1.

asymmetric synthesis - lactones - SAMP-hydrazones - α-alkylation - ozonolysis