InCl3/Me3SiBr-Catalyzed Direct Coupling between Silyl Ethers and Enol Acetates

A combined Lewis acid catalyst of InCl3 and Me3SiBr promoted the direct use of enol acetates in the coupling with low-reactive silyl ethers, in which functional groups including ketones and aldehydes survived. Sterically hindered silyl ethers such as ROSiEt3, ROSiPh3, ROSit-BuMe2, and ROSii-Pr3 were...

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Published inOrganic letters Vol. 13; no. 10; pp. 2762 - 2765
Main Authors Onishi, Yoshiharu, Nishimoto, Yoshihiro, Yasuda, Makoto, Baba, Akio
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.05.2011
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
LEWIS-ACID CATALYST
KETONES
SUBSTITUTION
B(C6F5)-CATALYZED ALLYLATION
ALDOL REACTION
ALPHA-ALKYLATION
CARBONYL-COMPOUNDS
ALLYLSILANES
TRIMETHYLSILYL ETHERS
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Summary:A combined Lewis acid catalyst of InCl3 and Me3SiBr promoted the direct use of enol acetates in the coupling with low-reactive silyl ethers, in which functional groups including ketones and aldehydes survived. Sterically hindered silyl ethers such as ROSiEt3, ROSiPh3, ROSit-BuMe2, and ROSii-Pr3 were also applicable.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol200875m