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Influence of enolate geometry on the stereochemistry of Michael additions of ketone enolates to α,β-unsaturated ketones

✍ Scribed by David A Oare; Clayton H Heathcock

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
207 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis

Preformed lithium enolates of ketones react with acyclic a,p-unsaturated ketones to give 1,5-diketones in good chemical yields.

A strong correlation exists between enolate geometry and product stereochemistry;

enolates having the z configuration provide anti addition products while E enolates usually provide the syn diastereomers.

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Influence of enolate geometry and struct
Influence of enolate geometry and structure on the stereochemistry of the asymmetric oxidation of prochiral ketone enolates to optically active α-hydroxy ketones
✍ Franklin A. Davis; Aurelia C. Sheppard; G.Sankar Lal 📂 Article 📅 1989 🏛 Elsevier Science 🌐 French ⚖ 309 KB

The sfereoselectiviry for the asymmetric oxidation of enolafes to opfica//y active a-hydroxy ketones using (+)-( camphoryisulfonyi)oxaziridine is dependent on the enoiate substitution pattern, the solution structure of the enoiate and to a lesser extent the enoiate geometry Optically active a-hydrox