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

Jianbo Zhang; Chinmoy Kumar Hazra; Sehoon Park; Sukbok Chang

doi:10.1002/ajoc.201900270

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

Jianbo Zhang, Chinmoy Kumar Hazra, Sehoon Park, Sukbok Chang^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	1637-1640
Number of pages	4
Journal	Asian Journal of Organic Chemistry
Volume	8
Issue number	9
DOIs	https://doi.org/10.1002/ajoc.201900270
State	Published - 1 Sep 2019
Externally published	Yes

Keywords

Carbocyclization
Cyclobutanes
Cyclopropanes
Hosomi-Sakurai reaction
Silylium ion catalysis

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10.1002/ajoc.201900270

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title = "Metal-Free Carbocyclization of Homoallylic Silyl Ethers Leading to Cyclopropanes and Cyclobutanes",

abstract = "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.",

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note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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doi = "10.1002/ajoc.201900270",

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T1 - Metal-Free Carbocyclization of Homoallylic Silyl Ethers Leading to Cyclopropanes and Cyclobutanes

AU - Zhang, Jianbo

AU - Hazra, Chinmoy Kumar

AU - Park, Sehoon

AU - Chang, Sukbok

PY - 2019/9/1

Y1 - 2019/9/1

N2 - 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.

AB - 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.

KW - Carbocyclization

KW - Cyclobutanes

KW - Cyclopropanes

KW - Hosomi-Sakurai reaction

KW - Silylium ion catalysis

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DO - 10.1002/ajoc.201900270

M3 - 文章

AN - SCOPUS:85068874909

SN - 2193-5807

VL - 8

SP - 1637

EP - 1640

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 9

ER -

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

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Keywords

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