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 |
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Pages (from-to) | 1637-1640 |
Number of pages | 4 |
Journal | Asian Journal of Organic Chemistry |
Volume | 8 |
Issue number | 9 |
DOIs | |
State | Published - 1 Sep 2019 |
Externally published | Yes |
Keywords
- Carbocyclization
- Cyclobutanes
- Cyclopropanes
- Hosomi-Sakurai reaction
- Silylium ion catalysis