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

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Title
Metal-Free Carbocyclization of Homoallylic Silyl Ethers Leading to Cyclopropanes and Cyclobutanes
Author(s)
Jianbo Zhang; Chinmoy Kumar Hazra; Sehoon Park; Sukbok Chang
Subject
Carbocyclization, ; Cyclobutanes, ; Cyclopropanes, ; Hosomi-Sakurai reaction, ; Silylium ion catalysis
Publication Date
2019-09
Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY, v.8, no.9, pp.1637 - 1640
Publisher
WILEY-V C H VERLAG GMBH
Abstract
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, WeinheimWe 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.
URI
https://pr.ibs.re.kr/handle/8788114/6868
DOI
10.1002/ajoc.201900270
ISSN
2193-5807
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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