Asymmetric Synthesis of Fused Tetrahydroquinolines via Intra­molecular Aza-Diels–Alder Reaction of ortho-Quinone Methide Imines

Fabian Hofmann; Cornelius Gärtner; Martin Kretzschmar; Christoph Schneider

doi:10.1055/a-1517-7515

Synthesis 2022; 54(04): 1055-1080
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

Fabian Hofmann

,

Cornelius Gärtner

,

Martin Kretzschmar

,

Christoph Schneider ∗

Abstract

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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 - tetrahydroquinolines

Full Text

References

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Supplementary Material

Supporting Information

Asymmetric Synthesis of Fused Tetrahydroquinolines via Intra­molecular Aza-Diels–Alder Reaction of ortho-Quinone Methide Imines

Asymmetric Synthesis of Fused Tetrahydroquinolines via Intramolecular Aza-Diels–Alder Reaction of ortho-Quinone Methide Imines