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Alistair Boyer

Alistair Boyer

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These papers have been cited ≥527 times and 13 of these papers have been cited at least 13 times (H-Index).
015 Total Synthesis: Oxonium Ylide Formation and Rearrangement of 1-Sulfonyl-1,2,3-Triazoles DOI Enantioselective Synthesis of (+)-Petromyroxol, Enabled by Rhodium-Catalyzed Denitrogenation and Rearrangement of a 1-Sulfonyl-1,2,3-Triazole
Alistair Boyer
J. Org. Chem, 2015, 80, 4771–4775
DOI: 10.1021/acs.joc.5b00399
  • The excellent photo of the sea lamprey was taken by Ted Lawrence, Great Lakes Fishery Commission [link].
  • This work has been cited: 12 times.

Petromyroxol is a non-racemic mixture of enantiomeric oxylipids isolated from water conditioned with larval sea lamprey. The (+)-antipode exhibits interesting biological properties but only 1 mg was isolated from >100000 L of water. Recently, transition metal-catalyzed denitrogenation of 1-sulfonyl-1,2,3-triazoles has emerged as a powerful strategy for the synthesis of value-added products, including efficient diastereocontrolled construction of tetrahydrofurans. This methodology enabled the rapid development of the first synthesis of (+)-petromyroxol in 9 steps and 20% overall yield from a readily accessible starting material.

J. Org. Chem, 2015, 80, 4771
014 Brønsted Acid Catalysis: Cyclopropanation DOI Synthesis of Cyclopropyl-Substituted Furans by Brønsted Acid Promoted Cascade Reactions
J Stephen Clark, Filippo Romiti, Kirsten F Hogg, Malai Haniti S A Hamid, Sven C Richter, Alistair Boyer, Joanna C Redman and Louis J Farrugia
Angew. Chem. Int. Ed., 2015, 54, 5744–5747
DOI: 10.1002/anie.201500625
  • ISI Hot Paper 2015
  • This work has been cited: 13 times.

Chloroacetic acid promotes an efficient and diastereoselective intramolecular cascade reaction of electron-deficient ynenones to deliver products featuring a 2,3,5-trisubstituted furan bearing a fused cyclopropyl substituent at the 5-position. Synthetically relevant polycyclic building blocks featuring various size rings and heteroatoms have been synthesized in high yield using this mild acid-catalysed reaction.

Angew. Chem. Int. Ed., 2015, 54, 5744
013 1-Sulfonyl-1,2,3-Triazoles: Oxonium Ylide Formation and Rearrangement DOI Rhodium(II)-Catalyzed Stereocontrolled Synthesis of 2-Tetrasubstituted Saturated Heterocycles from 1-Sulfonyl-1,2,3-triazoles
Alistair Boyer
Org. Lett., 2014, 16, 5878–5881
DOI: 10.1021/ol5028267
  • This work has been cited: 29 times.

Rhodium(II) acetate catalyzes the denitrogenative transformation of 4-substituted 1-sulfonyl-1,2,3-triazoles with pendent allyl and propargyl ethers and thioethers to onium ylides that undergo [2,3]-sigmatropic rearrangement to give 2-tetrasubstituted heterocycles with high yield and diastereoselectivity.

Org. Lett., 2014, 16, 5878
012 1-Sulfonyl-1,2,3-Triazoles: Oxonium Ylide Formation and Rearrangement DOI Rhodium(II)-Catalyzed Stereocontrolled Synthesis of Dihydrofuran-3-imines from 1-Tosyl-1,2,3-Triazoles
Alistair Boyer
Org. Lett., 2014, 16, 1660–1663
DOI: 10.1021/ol500309x
  • ISI Highly Cited Paper 2014, 2015
  • Highlighted on the organic-chemistry.org portal [Link]
  • Awarded the Dave Kelly Cup for presentation of this research at the 2013 Gregynog Synthesis Workshop
  • This work has been cited: 54 times.

Rhodium(II) acetate catalyzes the denitrogenative transformation of 5-substituted and 4,5-disubstituted 1-sulfonyl-1,2,3-triazoles with pendent allyl and propargyl ether motifs to oxonium ylides that undergo [2,3]-sigmatropic rearrangement to give substituted dihydrofuran-3-imines in high yield and diastereoselectivity.

Org. Lett., 2014, 16, 1660
011 Organocatalysis: Sulfur Catalysis DOI Organocatalytic Synthesis of Highly Substituted Furfuryl Alcohols and Amines
J Stephen Clark, Alistair Boyer, Anthony Aimon, Paloma Engel García, David M Lindsay, Andrew D F Symington, Yves Danoy
Angew. Chem. Int. Ed., 2012, 51, 12128–12131
DOI: 10.1002/anie.201207300
  • Invited presentation at the COST Action Meeting (CM0804), Izmir, Turkey
  • Invited presentation at the 2012 RSC Perkin Meeting, St. Andrews, UK
  • Highlighted as part of the Wiley Organocatalysis Hot Topic [Link]
  • Highlighted in SynFacts [Abstract]
  • This work has been cited: 30 times.

Tetrahydrothiophene (THT) is an efficient organocatalyst for the synthesis of highly substituted furfuryl products from readily-accessible electron-poor enynes under neutral conditions. This process is demonstrated to be applicable to a wide-range of nucleophiles and enynes; and can be incorporated in a domino organocatalysis sequence.

Angew. Chem. Int. Ed., 2012, 51, 12128
010 Rhodium Catalysis: Domino Reactions DOI Rhodium-Catalysed Domino Enantioselective Synthesis of Bicyclo[2.2.2]lactones
Alistair Boyer, Mark Lautens
Angew. Chem. Int. Ed., 2011, 50, 7346–7349
DOI: 10.1002/anie.201101773
  • Featured in ChemInform 2011, 42 [Link]
  • This work was presented at the 2011 CSC Chemistry Conference, Montreal, Canada [Abstract]
  • This work has been cited: 20 times.

Once... twice... three times a catalyst! We demonstrate a novel triple domino rhodium(I)-catalysed asymmetric transformation of substituted oxabicyclic alkenes into bicycle[2.2.2]lactones. The reaction proceeds with good yields and excellent levels of stereoselectivity in each of the 16 examples studied. Mechanistic investigations suggest that this process proceeds by rhodium catalysed asymmetric ring opening, allylic alcohol isomerisation and oxidation.

Angew. Chem. Int. Ed., 2011, 50, 7346
009 Rhodium Catalysis: Regiodivergent Resolution DOI Practical Asymmetric Synthesis of Bioactive Aminotetralins from a Racemic Precursor using a Regiodivergent Resolution
Robert Webster, Alistair Boyer, Matthew J Fleming, Mark Lautens
Org. Lett., 2010, 12, 5418–5421
DOI: 10.1021/ol1022239
  • Highlighted in SynFacts [Link]
  • This work has been cited: 36 times.

Catalyst-controlled asymmetric ring opening of a racemic oxabicyclic alkene leads to two readily separable regioisomeric products both in excellent ee. A cationic Rh catalyst, with added NH4BF4 to modulate reactivity, was required to obtain synthetically useful yields. The utility of each substituted aminotetralin product has been demonstrated by their conversion to different biologically relevant molecules in a highly efficient and practical manner.

Org. Lett., 2010, 12, 5418
008 Rhodium Catalysis: Domino Reactions DOI Domino Rhodium(I)-Catalysed Reactions for the Efficient Synthesis of Substituted Benzofurans and Indoles
Alistair Boyer, Naohiro Isono, Sebastian Lackner, Mark Lautens
Tetrahedron, 2010, 66, 6468–6482
DOI: 10.1016/j.tet.2010.05.106
  • Invited contribution in honour of Prof. Steven V. Ley's receipt of the 2009 Tetrahedron Prize
  • This work was presented at the 2010 CSC Chemistry Conference, Toronto, Canada
  • Featured in ChemInform [Link]
  • This work has been cited: 44 times.

Rhodium(I) catalysts promote the transformation of o-alkynyl phenols and anilines to the corresponding benzo[b]furans and indoles. The reaction is postulated to proceed via a transient 3-rhodium heterocycle intermediate, which can be trapped with suitable electrophiles to give poly-substituted heterocycles. In the case of mono-substituted electron-withdrawn electrophiles, excellent yield and selectivity for conjugate addition versus Heck/Mizoroki reaction can be achieved. In the case of 2-alkynyl pyridine electrophiles, novel 2-(benzofuran-3-yl)vinylpyridines are formed.

Tetrahedron, 2010, 66, 6468
007 Total Synthesis: Azadirachtin DOI Second-Generation Synthesis of Azadirachtin: A Concise Preparation of the Propargylic Mesylate Fragment
Alistair Boyer, Gemma E Veitch, Edith Beckmann, Steven V Ley
Angew. Chem. Int. Ed., 2009, 48, 1317–1320
DOI: 10.1002/anie.200805395
  • This work has been cited: 15 times.

A second bite of the apple: A new and highly efficient synthesis of the propargylic mesylate fragment of azadirachtin has been accomplished. An enantioselective catalytic hetero Diels-Alder reaction sets up the stereocenter at C15, which then controls the installation of the remaining functionality in a total of only 17 steps.

Angew. Chem. Int. Ed., 2009, 48, 1317
006 Total Synthesis: Azadirachtin DOI The Azadirachtin Story
Gemma E Veitch, Alistair Boyer, Steven V Ley
Angew. Chem. Int. Ed., 2008, 47, 9402–9429
DOI: 10.1002/anie.200802675
  • This work has been cited: 50 times.

Azadirachtin has been the subject of intensive research within the scientific community ever since its isolation from the neem tree in 1968. There are now over 1000 publications relating to this natural product which cover all aspects of structural, biological and synthetic studies. Herein, we describe the worldwide efforts towards the synthesis of this fascinating molecule.

Angew. Chem. Int. Ed., 2008, 47, 9402cover by Matt O'Brien
005 Total Synthesis: Azadirachtin DOI The Synthesis of Azadirachtin: A Potent Insect Antifeedant
Steven V Ley, et al. (show all...)
Chem. Eur. J., 2008, 14, 10683–10704
DOI: 10.1002/chem.200801103
  • This work has been cited: 34 times.

The final chapter! We describe in full the first synthesis of the potent insect antifeedant azadirachtin through a highly convergent approach. An O-alkylation reaction is used to unite decalin ketone and propargylic mesylate fragments, after which a Claisen rearrangement constructs the central C8-C14 bond in a stereoselective fashion. The allene which results from this sequence then enables a second critical carbon-carbon bond forming event whereby the [3.2.1] bicyclic system, present in the natural product, is generated via a 5-exo-radical cyclisation process. Finally, using knowledge gained through our early studies into the reactivity of the natural product, a series of carefully designed steps completes the synthesis of this challenging molecule.

Chem. Eur. J., 2008, 14, 10683cover by Alistair Boyer
004 Supercritical Carbon Dioxide DOI Clean and Efficient Synthesis of O-Silylcarbamates and Ureas in Supercritical Carbon Dioxide
Matthew J Fuchter, Catherine J Smith, Melanie W S Tsang, Alistair Boyer, Simon Saubern, John H Ryan, Andrew B Holmes
Chem. Commun., 2008, 2152–2154
DOI: 10.1039/b801537f
  • Featured in ChemInform [Link]
  • This work has been cited: 24 times.

The synthesis of a family of O-silylcarbamates from the corresponding silylamines has been achieved simply by heating the silylamine in supercritical carbon dioxide (scCO2), and these O-silylcarbamates have been shown to be effective precursors for the synthesis of a range of symmetrical and unsymmetrical ureas.

Chem. Commun., 2008, 0, 2152
003 Total Synthesis: Azadirachtin DOI Synthesis of Natural Products from the Indian Neem Tree Azadirachta Indica
Gemma E Veitch, Andrea Pinto, Alistair Boyer, Edith Beckmann, James C Anderson, Steven V Ley
Org. Lett., 2008, 10, 569–572
DOI: 10.1021/ol7027898
  • This work has been cited: 14 times.

The synthesis of five natural products isolated from the Indian neem tree Azadirachta indica, is reported from a common intermediate. The judicious choice of transacetalization conditions allows efficient access to both the azadirachtinin and the azadirachtin skeletons.

Org. Lett., 2008, 10, 569
002 Total Synthesis: Azadirachtin DOI A Relay Route for the Synthesis of Azadirachtin
Gemma E Veitch, Edith Beckmann, Brenda J Burke, Alistair Boyer, Carles Ayats, Steven V Ley
Angew. Chem. Int. Ed., 2007, 46, 7633–7635
DOI: 10.1002/anie.200703028
  • This work has been cited: 51 times.

22 Years in the making: Azadirachtin was synthesized for the first time by a highly convergent approach, utilizing a Claisen rearrangement and a radical cyclization as key steps. End-game strategies relied on a relay-intermediate, which could be obtained by synthetic methods as well as by degradation of the natural product.

Angew. Chem. Int. Ed., 2007, 46, 7633cover by Alistair Boyer
001 Total Synthesis: Azadirachtin DOI Synthesis of Azadirachtin: A Long but Successful Journey
Gemma E Veitch, Edith Beckmann, Brenda J Burke, Alistair Boyer, Sarah Maslen, Steven V Ley
Angew. Chem. Int. Ed., 2007, 46, 7629–7632
DOI: 10.1002/anie.200703027
  • This work has been cited: 97 times.

22 Years in the making: Azadirachtin was synthesized for the first time by a highly convergent approach, utilizing a Claisen rearrangement and a radical cyclization as key steps. End-game strategies relied on a relay-intermediate, which could be obtained by synthetic methods as well as by degradation of the natural product.

Angew. Chem. Int. Ed., 2007, 46, 7629cover by Alistair Boyer

Non-refereed contributions:

002 Organic Syntheses DOI Preparation of Horner-Wadsworth-Emmons Reagent: Methyl 2-Benzyloxycarbonylamino-2-(dimethoxyphosphinyl)-acetate
Submitters: Hiroki Azuma, Kentaro Okano, Tohru Fukuyama, Hidetoshi Tokuyama
Checkers: Alistair Boyer, Mark Lautens

Org. Synth., 2011, 88, 152–161
DOI: 10.15227/orgsyn.088.0152

Org. Synth., 2011, 88, 152
001 Organic Syntheses DOI Synthesis of Substituted Indazoles via [3+2] Cycloaddition of Benzyne and Diazo Compounds
Submitters: Feng Shi, Richard C Larock
Checkers: Alistair Boyer, Mark Lautens

Org. Synth., 2010, 87, 95–103
DOI: 10.15227/orgsyn.087.0095
  • This work has been cited: 4 times.

Benzyne is a highly reactive intermediate that has attracted wide attention from synthetic organic chemists. One of the commercially available precursors of benzyne is 2-(trimethylsilyl)phenyl trifluoromethanesulfonate which undergoes fluoride-promoted ortho-elimination to generate benzyne, mild conditions which tolerate a range of functional groups. Benzyne which is generated in this way has been shown to react with diazo compounds as 1,3-dipoles to afford substituted 1H-indazoles following a hydrogen shift.

Org. Synth., 2010, 87, 95

alistair@boyer-research.com

School of Chemistry
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University of Glasgow
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