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Synthesis 2022; 54(04): 1055-1080
DOI: 10.1055/a-1517-7515
DOI: 10.1055/a-1517-7515
special topic
Cycloadditions – Established and Novel Trends – in Celebration of the 70th Anniversary
of the Nobel Prize Awarded to Otto Diels and Kurt Alder
Asymmetric Synthesis of Fused Tetrahydroquinolines via Intramolecular Aza-Diels–Alder Reaction of ortho-Quinone Methide Imines
Generous financial support has been provided by the Deutsche Forschungsgemeinschaft (SCHN 441/11-2) and the Deutsche Bundesstiftung Umwelt (DBU) in the form of a predoctoral fellowship awarded to M.K.
Abstract
Aza-Diels–Alder reactions are straightforward processes for the construction of N-heterocycles, featuring inherent atom-economy and stereospecificity. Intramolecular strategies allow the formation of bicyclic core structures with up to three stereocenters within a single step. Herein, this concept is combined with the chemistry of chiral Brønsted acid bound ortho-quinone methide imines to generate a range of interesting fused tetrahydroquinolines in a diastereo- and enantioselective manner.
Key words
aza-Diels–Alder reactions - ortho-quinone methide imines - Brønsted acid catalysis - N-triflyl phosphoric amide - tetrahydroquinolinesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1517-7515.
- Supporting Information
Publication History
Received: 23 April 2021
Accepted after revision: 26 May 2021
Accepted Manuscript online:
26 May 2021
Article published online:
01 July 2021
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