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Stereoselective Synthesis of Highly-Congested Tetralin-Fused Spirooxindoles with Hydroxyl Group: Net Oxygen Atom Induced Hydride Shift/cyclization Process.

preprint
submitted on 19.05.2021, 08:47 and posted on 24.05.2021, 09:30 by Dan Sakai, mizuki machida, Keiji Mori
Highly stereoselective synthesis of tetralin-fused spirooxindoles with two contiguous stereogenic centers. In the present reaction, not only [1,5]-hydride shift/cyclization process, but also replacemnt of nitrogen atom to oxygen atom ocurred smoothly to give target structure with hydroxy grop in good chemical yields with good to excellent diastereoselectivities (up to d.r. = >20:1). Investigation of the reaction mechanism suggested that this “atom-replacement” event ocurred via the iminium cation intermediates.

History

Email Address of Submitting Author

k_mori@cc.tuat.ac.jp

Institution

Tokyo University of Agriculture and Technology

Country

Japan

ORCID For Submitting Author

0000-0002-9878-993X

Declaration of Conflict of Interest

There is no conflict of interest.