3-Metallated Enamines VI+. Use as β-Oxo Vinyl Anion Equivalents
| Main Authors: | C. S. SUDHEENDRANATH, H. AHLBRECHT |
|---|---|
| Format: | Article Journal |
| Bahasa: | eng |
| Terbitan: |
, 1981
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| Subjects: | |
| Online Access: |
https://zenodo.org/record/6379446 |
Daftar Isi:
- Fachbereich Chemie der Justus Liebig-Universitat Giessen Institut fur Organische Chemie, Heinrich-Buff-Ring 58, D-6300 Giessen, Bundesrepublik Deutschland Manuscript received 13 April 1981, accepted 11 August 1981 Two possibilities to produce a synthetic equivalent for the β-oxo vinyl anion starting from a saturated carbonyl compound are investigated. In the first method, a methylthio group is introduced into the 3-position of the corresponding enamine. Metallation, regioselective attack by an electrophile followed by hydrolysis and oxidative elimination of the methylthio group completes the sequence. In the second method, the trimethyl silyl group is introduced instead. After deprotonation and regioselective reaction with an electrophile, the silylated enamine is chlorinated with N-chlorosuccinimid. Dechiorosilylation and simultaneous hydrolysis of the enamine are achieved by means of trifluoro acetic acid/hydrochloric acid and sodium fluoride in ethanol.