Journal
MOLECULES
Volume 27, Issue 20, Pages -Publisher
MDPI
DOI: 10.3390/molecules27207138
Keywords
HWE reaction; Still-Gennari olefination; Ando olefination; stereoselective synthesis; Z-selectivity; Wittig reaction; phosphonates; alkenes; hexafluoroisopropanol; C=C bond formation
Funding
- Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences [500-02]
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This report presents new, easily accessible reagents for highly Z-selective HWE reactions, demonstrating very good Z-selectivity and high yields in most cases. The application of these new reagents may provide a valuable and practical alternative to the well-established Still-Gennari or Ando Z-selective carbonyl group olefination protocols.
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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