Highly <i>Z</i>-Selective Horner–Wadsworth–Emmons Olefination Using Modified Still–Gennari-Type Reagents

Highly <i>Z</i>-Selective Horner–Wadsworth–Emmons Olefination Using Modified Still–Gennari-Type Reagents

In this report, new, easily accessible reagents for highly <i>Z</i>-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. Ve...

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Bibliographic Details
Main Authors: Ignacy Janicki, Piotr Kiełbasiński
Format: Article
Language:English
Published: MDPI AG 2022-10-01
Series:Molecules
Subjects:
HWE reaction
Still-Gennari olefination
Ando olefination
stereoselective synthesis
<i>Z</i>-selectivity
Wittig reaction
Online Access:https://www.mdpi.com/1420-3049/27/20/7138
Description
Summary:In this report, new, easily accessible reagents for highly <i>Z</i>-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 <i>Z</i>-selectivity (up to a 98:2 <i>Z</i>:<i>E</i> 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 <i>Z</i>-selective carbonyl group olefination protocols.
ISSN:1420-3049

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