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2 article(s) from Whiting, Andrew

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

David R. Chisholm,
Garr-Layy Zhou,
Ehmke Pohl,
Roy Valentine and
Andrew Whiting

Beilstein J. Org. Chem. 2016, 12, 1851–1862, doi:10.3762/bjoc.12.174

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Graphical Abstract

Figure 1: Tetrahydroquinoline (THQ) and dihydroquinoline (DHQ) scaffolds to be synthesised.

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Scheme 1: Proposed retrosynthesis scheme to access N-isopropyl-THQ 2.

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Scheme 2: Synthesis of THQ 3 by initial N-alkylations, followed by PPA-mediated cyclisation.

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Scheme 3: Bromination of 3 and attempted halogen exchange of the intermediate 7.

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Scheme 4: Synthesis of THQ 10, by initial aza-Michael addition, followed by formation of the tertiary alcohol ...

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Scheme 5: Synthesis of THQ 14 by initial acylation, cyclisation with H₂SO₄ and reduction with borane·dimethyl...

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Scheme 6: N-Alkylation of 13 and 14.

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Scheme 7: Facile route for the synthesis of 20a.

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Scheme 8: Synthesis of THQ 21 and DHQ 22 using borane·dimethyl sulphide complex or DIBAL, respectively.

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Figure 2: Simulated structure of 22 indicates a flattened quinoline-like structure. Hartree–Fock calculations...

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Scheme 9: Postulated mechanism for the formation of 22 using DIBAL.

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Figure 3: Combined, normalised absorption and emission spectra of 28 in chloroform. Absorption spectrum was r...

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Scheme 10: Miyaura borylation of 21 and 22 to give crystalline boronic esters 29 and 30.

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Figure 4: Comparison of the crystal structures of 29 (left) and 30 (right) as viewed along the plane of the a...

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Figure 5: Combined, normalised absorption and emission spectra of 30 in diethyl ether. Absorption spectrum wa...

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Full Research Paper

Published 16 Aug 2016

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Boron-substituted 1,3-dienes and heterodienes as key elements in multicomponent processes

Ludovic Eberlin,
Fabien Tripoteau,
François Carreaux,
Andrew Whiting and
Bertrand Carboni

Beilstein J. Org. Chem. 2014, 10, 237–250, doi:10.3762/bjoc.10.19

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Scheme 1: 1-Boron-substituted 1,3-diene in a tandem cycloaddition [4 + 2]/allylboration sequence.

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Scheme 2: Lewis acid catalyst in the tandem cycloaddition [4 + 2]/allylboration sequence.

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Scheme 3: Synthesis of an advanced precursor of clerodin.

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Scheme 4: Intramolecular Diels–Alder/allylboration sequence.

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Scheme 5: Diastereoselective Diels–Alder reaction with N-phenylmaleimide and 4-phenyltriazoline-3,5-dione.

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Scheme 6: Asymmetric synthesis of a α-hydroxyalkylcyclohexane.

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Scheme 7: Tandem [4 + 2]-cycloaddition/allylboration of 3-silyloxy- and 4-alkoxy-dienyl boronates.

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Scheme 8: Metal-mediated cycloisomerization/Diels–Alder reaction/allylboration sequence.

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Scheme 9: Cobalt-catalyzed Diels–Alder/allylboration sequence.

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Scheme 10: A two-step reaction sequence for the synthesis of tetrahydronaphthalenes 12.

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Scheme 11: Tandem sequence based on the Petasis borono–Mannich reaction as first key step.

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Scheme 12: One-pot tandem dimerization/allylboration reaction of 1,3-diene-2-boronate.

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Scheme 13: Tandem Diels–Alder/cross-coupling reactions of trifluoroborates 15.

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Scheme 14: Diels–Alder/cross-coupling reactions of 16.

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Scheme 15: Metal catalyzed tandem Diels–Alder/hydrolysis reactions.

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Scheme 16: Synthesis of anti-1,5-diols 18 by triple aldehyde addition.

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Scheme 17: Catalytic enantioselective three-component hetero-[4 + 2]-cycloaddition/allylboration sequence.

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Scheme 18: Synthesis of natural products using the catalytic enantioselective HDA/allylboration sequence.

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Scheme 19: Total synthesis of a thiomarinol derivative.

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Scheme 20: Synthesis of an advanced intermediate 27 for the east fragment of palmerolide A.

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Scheme 21: Bicyclic piperidines from tandem aza-[4 + 2]-cycloaddition/allylboration.

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Scheme 22: Hydrogenolysis reactions of hydrazinopiperidines.

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Scheme 23: Tandem aza-[4 + 2]-cycloaddition/allylboration/retrosulfinyl-ene sequence.

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Scheme 24: Boronated heterodendralene 32 in [4 + 2]-cycloadditions.

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Scheme 25: Synthesis of tricyclic imides derivatives.

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Scheme 26: Synthesis of 37 via a HDA/allylboration/DA sequence.

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Scheme 27: Diels–Alder/allylboration sequence.

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Review

Published 22 Jan 2014

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