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Regioselective azidomethoxylation of enol ethers by anodic oxidation

✍ Scribed by Kazuo Fujimoto; Yuichiro Tokuda; Yoshiharu Matsubara; Hirofumi Maekawa; Takumi Mizuno; Ikuzo Nishiguchi

Book ID
103407641
Publisher
Elsevier Science
Year
1995
Tongue
French
Weight
245 KB
Volume
36
Category
Article
ISSN
0040-4039

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Oxidatkn of E-and Z-vinyl lithiums with silyl peroxides 5 affords silyl enol ethers 3 in good to excellent yield with retentton of configuration. This methodobgy represents a useful new procedure for the stereoand regbselective synthesis of ketone enolates.

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Abatraet: It has been shown that enol ether derived 2-phenyl-3-silyloxy-oxetanes 1 and 3 can be cleaved by catalytic hydrogenation. In combination with the preceding Patemb-Btichi reaction the method enables a regioselective access to 1,2diols 2 starting from oleftic substrates. Optionally, the redu