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Stereoselective kinetic protonation of chiral γ-lactone enolates

✍ Scribed by Seiichi Takano; Junko Kudo; Michiyasu Takahashi; Kunio Ogasawara

Book ID
104218623
Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
218 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 discrimination by chiral proton source is also observed in particular cases.

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