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Metal‐Free Carbocyclization of Homoallylic Silyl Ethers Leading to Cyclopropanes and Cyclobutanes
Author(s) -
Zhang Jianbo,
Hazra Chinmoy Kumar,
Park Sehoon,
Chang Sukbok
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900270
Subject(s) - chemistry , silylation , cyclobutanes , nucleophile , cyclopropane , cyclobutane , thioether , steric effects , lewis acids and bases , selectivity , medicinal chemistry , organic chemistry , stereochemistry , catalysis , ring (chemistry)
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.