✦ LIBER ✦
Regiospecific Intramolecular Aldol Condensation Induced by Conjugate Addition of lithium dimethylcuprate to ζ-Oxo-α, β-enones preliminary communication [1]
✍ Scribed by Ferdinand Näf; René Decorzant; Walter Thommen
- Book ID
- 102249648
- Publisher
- John Wiley and Sons
- Year
- 1975
- Tongue
- German
- Weight
- 463 KB
- Volume
- 58
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
ζ‐Oxo‐α, β‐enones react with lithium dimethylcuprate to give cyclic aldols such as hydroxydecalone 1 and hydroxyspiro[4.5]decanone 2 in a regio‐ and stereospecific manner. This new reaction, a combination of conjugate methyl addition to α, β‐enones with directed intramolecular aldolisation, is suggested to proceed via either enoate anions, such as 8 and 11, or radical anions, such as 9 → 10 and 12 → 13, as intermediates.