𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Enolization of γ-Lactones

✍ Scribed by Prof. Dr. W. Theilacker; Dr. K.-H. Bremer; Dr. L. Seidil

Book ID
101543662
Publisher
John Wiley and Sons
Year
1964
Tongue
English
Weight
103 KB
Volume
3
Category
Article
ISSN
0044-8249

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When lithium enolates generated from five chiral c,Y-disubstituted Y-lactones are treated with proton sources, formation of the u,Y-syn epimers always predominates over the a,Y-anti epimers in ratios of 10.2-2.9:l. Higher syn/anti ratios are obtained via silyl enolates in some cases. Chirality discr

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This investigation began in an attempt to develop an efficient new synthetic method for the stereospecific synthesis of the Y-alkylidena double bond in the sesquiterpene, freelingyne, I (1). Although methods are avsilable for the preparation of enol la&ones they usually lack stereochemical control.