Intramolecular Aza-Diels-Alder Reactions of ortho-Quinone Methide Imines: Rapid, Catalytic, and Enantioselective Assembly of Benzannulated Quinolizidines

Angewandte Chemie
Martin KretzschmarChristoph Schneider

Abstract

Aza-Diels-Alder reactions (ADARs) are powerful processes that furnish N-heterocycles in a straightforward fashion. Intramolecular variants offer the additional possibility of generating bi- and polycyclic systems with high stereoselectivity. We report herein a novel Brønsted acid catalyzed process in which ortho-quinone methide imines tethered to the dienophile via the N substituent react in an intramolecular ADAR to form complex quinolizidines and oxazinoquinolines in a one-step process. The reactions proceed under very mild conditions, with very good yields and good to very good diastereo- and enantioselectivities. Furthermore, the process was extended to a domino reaction that efficiently combines substrate synthesis, ortho-quinone methide imine formation, and ADAR.

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Citations

Oct 3, 2018·Chemical Communications : Chem Comm·Renjie ChenSunliang Cui
Jan 1, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Bo Reum SongSeung-Mann Paek
Mar 3, 2020·Chemistry : a European Journal·Riccardo SalvioMarco Bella
Apr 27, 2021·Organic & Biomolecular Chemistry·Lu LeiDong-Liang Mo
Oct 23, 2018·The Journal of Organic Chemistry·Anton S MakarovVladimir Gevorgyan
Nov 2, 2021·Organic & Biomolecular Chemistry·Guillermo Caballero-García, Jonathan M Goodman

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