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New methods for the stereoselective synthesis of 2-hydroxy-3,4-dienoates and functionalized 2,5-dihydrofurans

✍ Scribed by Norbert Krause; Michael Laux; Anja Hoffmann-Röder

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
59 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

Titanium enolates of 3,4-dienoates 3 were formed by treatment with LDA and Cp 2 TiCl 2 and oxidized with dimethyl dioxirane to furnish the allenic hydroxyesters 4 with up to 90% diastereoselectivity. Smooth cyclization to the functionalized 2,5-dihydrofurans 5 was accomplished with complete axis to center chirality transfer by treatment with HCl gas in chloroform.

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