|Title:||Synthesis of Polycyclic Spirocarbocycles via Acid-Promoted Ring-Contraction/Dearomative Ring-Closure Cascade of Oxapropellanes|
Takikawa, Hiroshi https://orcid.org/0000-0002-4414-2129 (unconfirmed)
Takasu, Kiyosei https://orcid.org/0000-0002-1798-7919 (unconfirmed)
|Author's alias:||小川, 直希|
|Publisher:||American Chemical Society (ACS)|
|Journal title:||Organic letters|
|Abstract:||We report herein the development of an acid-promoted rearrangement of oxa[4.3.2]propellanes to afford polyaromatic-fused spiro[4.5]carbocycles. DFT calculations suggest that the reaction pathway involves generation of a cyclobutyl cation, ring contraction to the cyclopropylcarbinyl cation, and dearomative ring closure by an internal 2-naphthol moiety. The resulting spirocarbocycles are synthetically valuable, as they could be transformed into two different polycyclic aromatic hydrocarbons via skeletal rearrangement. Syntheses of optically pure spirocarbocycles via a central-to-axial-to-central chirality transfer are also described.|
|Rights:||This document is the Accepted Manuscript version of a Published Work that appeared in final form in 'Organic letters', copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.9b02835.|
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|Appears in Collections:||Journal Articles|
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