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Highly stereoselective formation of enol silyl ethers

✍ Scribed by Eiichi Nakamura; Koichi Hashimoto; Isao Kuwajima

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

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✦ Synopsis

While regiochemical aspects of enolate chemistry have been studied

extensively, 1 virtually no attention has been paid until recently to geometry of the double bond of enolate anions.

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Phenylthiomethylstannylation of silyl en
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Silyl enol ethers (2) react with trihutyl [(phenylthio) chloromethyl] stannane (1) in the presence of Zinc bromide to give B-phenylthiomethylstannyl ketones (3) in good yields. Silyl dienol ethers (4) mainly give products (5) due to y-attack, under these conditions. S-Stannyl Carbonyl compounds have

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Mn-cnolam are easily and quandtattvciy abtakd under mild mt&io~~ (THF. -1OaC to rt. Ih) by tmument C# ketones with tmmatic Mn-ami&.s such as Ph(Me)NMnZ. They allow to prepare 2 siiyl en01 ethers ami 2 emi esters in hi (kinetic product: 2 99%. ZIE: 9317 to 1001 d h yitlds and with an excdent regio-an