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Highly Z-Selective Horner-Wadsworth-Emmons Olefination Using Modified Still-Gennari-Type Reagents
Ignacy Janicki1, Piotr Kiełbasiński1
1Division of Organic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland.
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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