Lewis Acid Catalyzed Intramolecular [4+2] Cycloaddition of In Situ Generated Aza‐Quinone Methides for the Stereoselective Synthesis of Furo/pyrano[3,2‐<i>c</i>]tetrahydroquinolines

Gharpure, Santosh J.; Vishwakarma, Dharmendra S.

doi:10.1002/ejoc.201901598

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2022

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Cited by 6 publications

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Formal [4+2] Cycloaddition of o‐Aza‐Quinone Methide for the Synthesis of 1,4‐Heterocycle‐Fused Quinolines

2021

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A protocol involving intramolecular formal [4 + 2]-cycloaddition of in situ generated o-azaquinone methide for the facile synthesis of 1,4heterocycle-fused quinoline motifs is demonstrated. The cascade involved tandem CÀ O, CÀ C, and CÀ N bond formation and also exhibited excellent functional group tolerance. Enantiomerically enriched 1,4-oxazepino quinolines were synthesized using alkynols derived from L-amino acids. The sulfoxide embedded quinolines were transformed to pentacyclic 1,4-thiepino tethered indeno-quinoline scaffolds via Pummerer cyclization.

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Formal [4+2] Cycloaddition of o‐Aza‐Quinone Methide for the Synthesis of 1,4‐Heterocycle‐Fused Quinolines

2021

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Enantioselective Synthesis of Spiro Chroman‐Isoindolinones via Formal (4+2) Cycloaddition of In Situ‐Generated ortho‐Quinone Methides with 3‐Methylene Isoindolinones

2022

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Using chiral phosphoric acids as organocatalysts, a formal asymmetric (4+2) cycloaddition of 3‐methylene isoindolinone and in situ‐generated ortho‐quinone methide substrates is disclosed. This reaction exhibited a broad substrate scope with various substituted cyclic enamides and ortho‐hydroxybenzyl alcohol derivatives to construct a series of spiro chroman‐isoindolinones containing spiro‐N,O‐heterocycles with 56 to 93% ee. This strategy demonstrates significant potential towards establishing a chiral spiro‐N,O‐aminal systems bearing two chiral carbon centers, including a tetrasubstituted carbon stereocenter.

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Six-membered ring systems: with O and/or S atoms

Santos

Silva

2021

Progress in Heterocyclic Chemistry

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Lewis Acid Catalyzed Intramolecular [4+2] Cycloaddition of In Situ Generated Aza‐Quinone Methides for the Stereoselective Synthesis of Furo/pyrano[3,2‐c]tetrahydroquinolines

Cited by 6 publications

References 55 publications

Formal [4+2] Cycloaddition of o‐Aza‐Quinone Methide for the Synthesis of 1,4‐Heterocycle‐Fused Quinolines

Formal [4+2] Cycloaddition of o‐Aza‐Quinone Methide for the Synthesis of 1,4‐Heterocycle‐Fused Quinolines

Enantioselective Synthesis of Spiro Chroman‐Isoindolinones via Formal (4+2) Cycloaddition of In Situ‐Generated ortho‐Quinone Methides with 3‐Methylene Isoindolinones

Six-membered ring systems: with O and/or S atoms

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