Stereoselective synthesis of 2,3-epoxy alcohols mediated by a remote sulfinyl group |
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Authors: | José Luis García Ruano Ana M Martín-Castro Francisco Tato M Giovanna Tocco Saverio Florio Vito Capriati |
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Institution: | a Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain b Dipartimento Farmaco-Chimico, Università degli Studi di Bari, 70126 Bari, Italy |
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Abstract: | The influence of the sulfinyl group as a chiral auxiliary in the stereoselective addition of oxiranyllithiums to (S)-2-p-tolylsulfinylbenzaldehyde has been studied. All reactions evolve with retention of configuration at the starting lithiated carbon. Completely stereoselective additions have been observed when configurations at sulfur and the lithiated carbon are different (matched pair), whereas variable dr's values (ranging between 52:48 and >99:<1%) when they are identical (mismatched pair). |
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