Synlett 1989; 1989(1): 24-25
DOI: 10.1055/s-1989-34686
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Asymmetric 1,2- and 1,3-Inductions and Solvent Dependence Found in Chelate-Controlled Additions of Grignard Reagents and Cuprates to Chiral β-Formyl Esters. Stereoselective Synthesis of γ-Lactones

Agnes Janowitz* , Thomas Kunz, Gabriele Handke, Hans-Ulrich Reissig
  • *Institut für Organische Chemie der Technischen Hochschule Darmstadt, Petersenstrasse 22, D-6100 Darmstadt, Federal Republic of Germany
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Publication History

Publication Date:
26 February 2002 (online)

The stereoselectivity of cuprate or Grignard reagent additions to chiral β-formyl esters 1, 3, and 5 highly depends on the solvent employed. Also, the substitution pattern of the aldehyde determines whether the cis- or trans-γ-lactone is the major product.