Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 17, Pages 4774-4778Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201800787
Keywords
asymmetric synthesis; Bronsted acid catalysis; nitrogen heterocycles; organocatalysis; quinone methide imines
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Funding
- Deutsche Forschungsgemeinschaft [SCHN 441/11-2]
- Deutsche Bundesstiftung Umwelt (DBU)
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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 Bronsted 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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