Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
Org Lett. 2022 Dec 30;24(51):9497-9501. doi: 10.1021/acs.orglett.2c03978. Epub 2022 Dec 15.
Oxygenated-1,2-cyclohexadienes and their unsubstituted counterpart can be generated under mild conditions by fluoride-induced desilylation and undergo intermolecular [2 + 2]-cycloaddition reactions with a variety of alkene traps to afford bicyclo[4.2.0]octenes. Both styrenes and electron-deficient olefins react in good conversion and with complete regioselectivity in favor of cyclobutane formation at the unsubstituted C2/C3 carbons of the C1-substituted cyclic allenes. Diastereoselectivities are modest (1.1-5.7:1) with a preference for the -isomer.
氧代-1,2-环己二烯及其未取代的同类物可以在温和条件下通过氟化物诱导的脱硅作用生成，并与各种烯烃捕获剂发生分子间[2+2]-环加成反应，生成双环[4.2.0]辛烯。苯乙烯和缺电子烯烃都以良好的转化率反应，并且具有完全的区域选择性，有利于在 C1 取代的环烯丙基的未取代 C2/C3 碳原子上形成环丁烷。非对映选择性适中（1.1-5.7:1），偏爱 -异构体。
