Highly Z-Selective Horner–Wadsworth–Emmons Olefination Using Modified Still–Gennari-Type Reagents |
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Authors: | Ignacy Janicki,Piotr Kieł basiń ski |
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Affiliation: | Division of Organic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland |
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Abstract: | In this report, new, easily accessible reagents for highly Z-selective HWE reactions are presented. Alkyl di-(1,1,1,3,3,3-hexafluoroisopropyl)phosphonoacetates, structurally similar to Still–Gennari type reagents, were tested in HWE reactions with a series of various aldehydes. Very good Z-selectivity (up to a 98:2 Z:E ratio) was achieved in most cases along with high yields. Application of the new reagents may be a valuable, practical alternative to the well-established Still–Gennari or Ando Z-selective carbonyl group olefination protocols. |
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Keywords: | HWE reaction Still-Gennari olefination Ando olefination stereoselective synthesis Z-selectivity Wittig reaction phosphonates alkenes hexafluoroisopropanol C=C bond formation |
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