Aiswarya Mini, Het Vyas, Ashvin J. Gangani, Matthew Melada, Anthony Shin and Abhishek Sharma*,
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引用次数: 0
Abstract
Ketyl radical-mediated ring opening and [2σ+2π] cycloaddition of cyclopropyl ketones (CPKs) with alkynes typically require activation by alkyl, aryl, or carbonyl groups yielding cyclopentenes having one or two non-adjacent stereocenters. We developed a one-pot multicomponent reaction of diboryl-activated CPKs with alkynes and aldehydes that merges ketyl radical chemistry with allylboration. This method enabled highly diastereoselective access to densely functionalized cyclopentenes featuring homoallylic alcohol, ketone, and alkenyl boronate motifs on adjacent quaternary, tertiary, and secondary stereogenic centers. Additionally, diboryl CPKs also allowed the synthesis of rare ketone-functionalized γ,γ-disubstituted allylic diborons.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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