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2 article(s) from White, Andrew J P

A combinatorial approach to improving the performance of azoarene photoswitches

Joaquin Calbo,
Aditya R. Thawani,
Rosina S. L. Gibson,
Andrew J. P. White and
Matthew J. Fuchter

Beilstein J. Org. Chem. 2019, 15, 2753–2764, doi:10.3762/bjoc.15.266

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Figure 1: a) Tetra ortho-substituted azobenzenes represent a significant advance in terms of Z-isomer stabili...

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Figure 2: Minimum-energy geometry calculated for a) the Z-isomer ground state and b) the transition states wi...

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Figure 3: Noncovalent index (NCI) surfaces calculated for representative pyrrolidine-based ortho-substituted ...

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Figure 4: Noncovalent index (NCI) surfaces and θ dihedral angles (in red) calculated for the minimum-energy g...

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Figure 5: Description of the lowest-lying n–π* excitation for the Z-isomers of halogenated 4pzH-F2 and 4pzH-C...

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Figure 6: Description of the lowest-lying n–π* excitation for the E-isomers of halogenated 4pzH-F2 and 4pzH-C...

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Figure 7: X-ray structures of 4pzMe-F2 (left), 4pzH-F2 (middle) and 4pzMe-OMe2 (right).

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Figure 8: Experimental UV–vis spectra of 4pzMe-F2, 4pzMe-Cl2, 4pzMe-OMe2 and 4pzH-F2 in MeCN at 25 µM.

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Published 14 Nov 2019

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Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction

Elizabeth P. Jones,
Peter Jones,
Andrew J. P. White and
Anthony G. M. Barrett

Beilstein J. Org. Chem. 2011, 7, 1570–1576, doi:10.3762/bjoc.7.185

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Scheme 1: 3-Component coupling reactions of arynes. E⁺ = electrophile.

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Scheme 2: Aryne mediated α-arylation of amino acids. DMG = directed metallation group. BHT = 2,6-di-tert-buty...

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Scheme 3: Proposed mechanism of α-arylation.

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Scheme 4: Proposed extension of the methodology to synthesize quaternary adducts.

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Scheme 5: Formation of α-methyl, α-aryl Schöllkopf adduct.

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Figure 1: NOESY correlation observed for 6a.

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Figure 2: X-ray crystal structure of 6b.

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Figure 3: Transition state analysis to explain the lack of diastereoselectivity at C-2.

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Scheme 6: Formation of quaternary adducts.

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Scheme 7: Hydrolysis of quaternary adducts.

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Scheme 8: Hydrolysis to amino acids.

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Scheme 9: Hydrolysis of analogue 6j.

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Scheme 10: Epimerization at C-3 of 6g.

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Published 25 Nov 2011

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