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Synthesis 2019; 51(11): 2359-2370
DOI: 10.1055/s-0037-1610685
DOI: 10.1055/s-0037-1610685
paper
Palladium-Catalyzed Decarboxylative [4+2] Cycloaddition of Vinyl Benzoxazinanones with Cyclic N-Sulfimines: Stereoselective Synthesis of Benzosulfamidate-Fused Tetrahydroquinazolines
This research was supported by the Nanomaterial Technology Development Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning (NRF-2012M3A7B4049645), and the Basic Science Research Program through the NRF funded by the Ministry of Education (NRF-2016R1D1A1A09916621).Weitere Informationen
Publikationsverlauf
Received: 21. November 2018
Accepted after revision: 28. Dezember 2018
Publikationsdatum:
20. Februar 2019 (online)
Abstract
Methods for the catalytic synthesis of highly functionalized benzosulfamidate-fused tetrahydroquinazolines are presented. The decarboxylative [4+2] cycloaddition of vinyl benzoxazinanones with benzoxathiazine 2,2-dioxides catalyzed by Pd(PPh3)4 affords fused-tetrahydroquinazolines with high diastereoselectivities. Alternatively, catalytic asymmetric [4+2] cycloaddition employing a chiral palladium-containing phosphoramidite ligand provides optically enriched benzosulfamidate-fused tetrahydroquinazolines in good yields and with excellent diastereoselectivities and enantioselectivities.
Key words
asymmetric catalysis - cycloaddition - vinyl benzoxazinanones - cyclic N-sulfimines - palladiumSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610685.
- Supporting Information
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