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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| Format: | Article |
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MDPI AG
2022-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/20/7138 |
| _version_ | 1797470753755496448 |
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| author | Ignacy Janicki Piotr Kiełbasiński |
| author_facet | Ignacy Janicki Piotr Kiełbasiński |
| author_sort | Ignacy Janicki |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-09T19:41:24Z |
| format | Article |
| id | doaj.art-6d83e206e2a24f6594dd96e808e2327c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T19:41:24Z |
| publishDate | 2022-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-6d83e206e2a24f6594dd96e808e2327c2023-11-24T01:38:11ZengMDPI AGMolecules1420-30492022-10-012720713810.3390/molecules27207138Highly <i>Z</i>-Selective Horner–Wadsworth–Emmons Olefination Using Modified Still–Gennari-Type ReagentsIgnacy Janicki0Piotr Kiełbasiński1Division of Organic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, PolandDivision of Organic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, PolandIn 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.https://www.mdpi.com/1420-3049/27/20/7138HWE reactionStill-Gennari olefinationAndo olefinationstereoselective synthesis<i>Z</i>-selectivityWittig reaction |
| spellingShingle | Ignacy Janicki Piotr Kiełbasiński Highly <i>Z</i>-Selective Horner–Wadsworth–Emmons Olefination Using Modified Still–Gennari-Type Reagents Molecules HWE reaction Still-Gennari olefination Ando olefination stereoselective synthesis <i>Z</i>-selectivity Wittig reaction |
| title | Highly <i>Z</i>-Selective Horner–Wadsworth–Emmons Olefination Using Modified Still–Gennari-Type Reagents |
| title_full | Highly <i>Z</i>-Selective Horner–Wadsworth–Emmons Olefination Using Modified Still–Gennari-Type Reagents |
| title_fullStr | Highly <i>Z</i>-Selective Horner–Wadsworth–Emmons Olefination Using Modified Still–Gennari-Type Reagents |
| title_full_unstemmed | Highly <i>Z</i>-Selective Horner–Wadsworth–Emmons Olefination Using Modified Still–Gennari-Type Reagents |
| title_short | Highly <i>Z</i>-Selective Horner–Wadsworth–Emmons Olefination Using Modified Still–Gennari-Type Reagents |
| title_sort | highly i z i selective horner wadsworth emmons olefination using modified still gennari type reagents |
| topic | HWE reaction Still-Gennari olefination Ando olefination stereoselective synthesis <i>Z</i>-selectivity Wittig reaction |
| url | https://www.mdpi.com/1420-3049/27/20/7138 |
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