Metal-Free Carbocyclization of Homoallylic Silyl Ethers Leading to Cyclopropanes and Cyclobutanes

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We have developed a Hosomi-Sakurai type carbocyclization of homoallylic silyl ethers in reaction with silyl nucleophiles, catalyzed by Lewis acidic silylium salt. It offers cyclopropane and cyclobutane products with high efficiency and selectivity. A range of silyl nucleophiles could be engaged in this transformation to give small-sized carbocycles incorporating allyl, allenyl, carbonyl, indole or thioether groups. Diastereoselectivity in the cyclobutane formation was observed to be dependent on the steric bulkiness of incoming nucleophiles.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2019-09
Language
English
Article Type
Article
Citation

ASIAN JOURNAL OF ORGANIC CHEMISTRY, v.8, no.9, pp.1637 - 1640

ISSN
2193-5807
DOI
10.1002/ajoc.201900270
URI
http://hdl.handle.net/10203/270060
Appears in Collection
CH-Journal Papers(저널논문)
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