𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Y-alkylation of lithium dienolates derived from 3(2h)-furanones and related α, β-unsaturated carbonyl compounds

✍ Scribed by Amos B. Smith III; Robert M. Scarborough Jr.

Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
242 KB
Volume
19
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

Although it is now generally accepted that lithium dienolates undergo near exclusive alkylation at the a rather than the y carbon, 1 we will demonstrate in this letter that, at least, for some 8-alkoxy-a,@-unsaturated carbonyl compounds, subtle structural features can markedly effect the a-selectivity. Our interest in the alkylation of 8-alkoxy-a,B-unsaturated carbonyl compounds arose in connection with 2,3 our studies directed at devising approaches to antitumor agents such as jatrophone, which possess the 3(2H)-furanone ring system. The results of this study are illustrated in Table I.

Initially we examined the alkylation of the kinetic enolate derived from 2,5dimethyl-3(2H)-furanone(l)via treatment with LDA in THF at -76OC. As expected alkylation occurred exclusively at the a'-position.

4 To our surprise however, alkyla-

📜 SIMILAR VOLUMES

ChemInform Abstract: Synthesis of 3,4-Di
ChemInform Abstract: Synthesis of 3,4-Dihydro-2H-benzopyrans from Phenols and α,β-Unsaturated Carbonyl Compounds.
✍ Hiroyuki Saimoto; Yoshie Ogo; Mie Komoto; Minoru Morimoto; Yoshihiro Shigemasa 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 34 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

ChemInform Abstract: β-Oxy-α-diazo-carbo
ChemInform Abstract: β-Oxy-α-diazo-carbonyl Compounds. Part 6. Synthesis and Reactivity of 3-Deoxy-2-diazo-esters Derived from Monosaccharides. Applications in the Synthesis of 2-C-Alkyl-KDO Analogues and Related Compounds.
✍ Francisco Sarabia; Fidel Jorge Lopez-Herrera 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 40 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v