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 journalArticlepeer-review

2 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 languageEnglish
Pages (from-to)1637-1640
Number of pages4
JournalAsian Journal of Organic Chemistry
Volume8
Issue number9
DOIs
StatePublished - 1 Sep 2019
Externally publishedYes

Keywords

  • Carbocyclization
  • Cyclobutanes
  • Cyclopropanes
  • Hosomi-Sakurai reaction
  • Silylium ion catalysis

Fingerprint

Dive into the research topics of 'Metal-Free Carbocyclization of Homoallylic Silyl Ethers Leading to Cyclopropanes and Cyclobutanes'. Together they form a unique fingerprint.

Cite this