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Synlett 1999; 1999(5): 629-631
DOI: 10.1055/s-1999-2665
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Asymmetric Synthesis of α-Substituted β-Formyl δ-Lactones via a Michael Addition/α-Alkylation Protocol

D. Enders* , J. Vázquez
  • *Institut für Organische Chemie, Professor-Pirlet-Str. 1, 52074 Aachen, Germany; Fax +49(2 41)8 88 81 27; E-mail: enders@RWTH-Aachen.de
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Publication Date:
31 December 1999 (online)

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An efficient trans-diastereo- and enantioselective synthesis of α-substituted β-formyl δ-lactones 5 (de ≥ 98%, ee = 80-95%) is described, employing formaldehyde-SAMP-hydrazone (1) as a neutral formyl anion equivalent. The new procedure involves the Michael addition of 1 to 5,6-dihydro-2H-pyran-2-one (2) followed by trans-selective α-alkylation and subsequent oxidative cleavage of the auxiliary.

SAMP-hydrazone - formyl anion equivalent - alkylation of lactones - Michael addition - asymmetric synthesis

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