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The Lindsay LAB

PUBLICATIONS

Lindsay Lab

(NC State University)

(25) Machín Rivera, R.; Ferrin, Z. R.; Lindsay, V. N. G. Org. Lett. 2024, 26, 4738-4743.
'Iron-Catalyzed Oxidative Rearrangement of Cyclopropanone Hemiaminals: General Access to Pyrroloindolones from Indoles.'

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(24) Jang, Y.; Deng, W.; Sprague, I. S.; Lindsay, V. N. G. Org. Lett. 2023, 25, 5389-5394.
'Divergent Synthesis of β-Fluoroamides via Silver-Catalyzed Oxidative Deconstruction of Cyclopropanone Hemiaminals.'

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(23) Jung, M.; Muir, J. E.; Lindsay, V. N. G. Tetrahedron 2023, 134, 133296.
'Expedient Synthesis of Spiro[3.3]heptan-1-ones via Strain-Relocating Semipinacol Rearrangements.'
Invited contribution in honor of Prof. John Wood - Selected as part of Tetrahedron's 2022 Editors' Choice Collection

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(22) Machín Rivera, R.; Burton, N. R.; Call, L. D.; Tomat, M. A.; Lindsay, V. N. G. Org. Lett. 2022, 24, 4275-4280.
'Synthesis of Highly Congested Tertiary Alcohols via the [3,3] Radical Deconstruction of Breslow Intermediates.'
Previously posted on ChemRxiv. Preprint: https://doi.org/10.26434/chemrxiv-2022-l60sc.

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(21) Jung. M.; Lindsay, V. N. G. J. Am. Chem. Soc. 2022, 144, 4764-4769.
'One-Pot Synthesis of Strain-Release Reagents from Methyl Sulfones'.

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(20) Penn, K. R.; Anders, E. J.; Lindsay, V. N. G. Organometallics 2021, 40, 3871-3875.
'Expedient Synthesis of Bis(imidazolium) Dichloride Salts and Bis(NHC) Complexes from Imidazoles Using DMSO as a Key Polar Additive'.
One of the three most read papers in Organometallics in December 2021.
Previously posted on ChemRxiv. Preprint: https://doi.org/10.33774/chemrxiv-2021-4h434.

(19) Poteat, C. M.; Lindsay, V. N. G. Org. Lett. 2021, 23, 6482-6487.
'Stereospecific Synthesis of Enantioenriched Alkylidenecyclobutanones via Formal Vinylidene Insertion into Cyclopropanone Equivalents'.
Previously posted on ChemRxiv. Preprint: https://doi.org/10.33774/chemrxiv-2021-kv6gx.

(18) Jang, Y.; Machín Rivera, R.; Lindsay, V. N. G. Synthesis 2021, 53, 3909-3934.
'Synthesis and Applications of Cyclopropanones and their Equivalents as Three-Carbon Building Blocks in Organic Synthesis'. (Review, invited contribution)

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(17) Jang, Y.; Lindsay, V. N. G. Org. Lett. 2020, 22, 8872-8876.
'Synthesis of Cyclopentenones with Reverse Pauson-Khand Regiocontrol via Ni-Catalyzed C–C Activation of Cyclopropanone'.
Previously posted on ChemRxiv. Preprint: https://doi.org/10.26434/chemrxiv.13012895.v1

(16) Machín Rivera, R.; Jang, Y.; Poteat, C. M.; Lindsay, V. N. G. Org. Lett. 2020, 22, 6510-6515.
'General Synthesis of Cyclopropanols via Organometallic Addition to 1-Sulfonylcyclopropanols as Cyclopropanone Precursors'.
Previously posted on ChemRxiv. Preprint: https://doi.org/10.26434/chemrxiv.12644153

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(15) Poteat, C. M.; Jang, Y.; Jung, M.; Johnson, J. D.; Williams, R. G.; Lindsay, V. N. G. Angew. Chem. Int. Ed. 2020, 59, 18655-18661.
'Enantioselective Synthesis of Cyclopropanone Equivalents and Application to the Formation of Chiral β-Lactams'.
Previously posted on ChemRxiv. Preprint: https://doi.org/10.26434/chemrxiv.11457909.v1

(14) Zhu, J.; Lindsay, V. N. G. ACS Catal. 2019, 9, 6993-6998 .
‘Benzimidazolyl Palladium Complexes as Highly Active and General Bifunctional Catalysts in Sustainable Cross-Coupling Reactions’.

(13) Poteat, C. M.; Lindsay, V. N. G. Chem. Commun. 2019, 55, 2912-2915.
‘Controlled α-mono- and α,α-di-halogenation of alkyl sulfones using reagent–solvent halogen bonding’.

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Postdoctoral

(UC Berkeley, with Prof. Richmond Sarpong)

(12) Lindsay, V. N. G.; Murphy, R. A.; Sarpong, R. Chem. Commun. 2017, 53, 10291-10294.
‘Effect of protic additives in Cu-catalysed asymmetric Diels-Alder cycloadditions of doubly activated dienophiles: towards the synthesis of magellanine-type Lycopodium alkaloids’.

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(11) Johnson, R. E.; de Rond, T.; Lindsay, V. N. G.; Keasling, J. D.; Sarpong, R. Org. Lett. 2015, 17, 3474-3477.
‘Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture’. (Featured in ACS Editors’ Choice)

(10) Lindsay, V. N. G.; Viart, H. M.-F.; Sarpong, R. J. Am. Chem. Soc. 2015, 137, 8368-8371.
‘Stereodivergent Intramolecular C(sp3)-H Functionalization of Azavinyl Carbenes: Synthesis of Saturated Heterocycles and Fused N-Heterotricycles’.

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(9) Schultz, E. E.; Lindsay, V. N. G.; Sarpong, R. Angew. Chem. Int. Ed. 2014, 53, 9904-9908.
‘Expedient Synthesis of Fused Azepine Derivatives using a Sequential Rhodium(II)-Catalyzed Cyclopropanation/1-Aza-Cope Rearrangement of Dienyltriazoles’.

doctoral

(Université de Montréal, with Prof. André B. Charette)

(8) Lindsay, V. N. G.; Fiset, D.; Gritsch, P. J.; Azzi, S.; Charette, A. B. J. Am. Chem. Soc. 2013, 135, 1463-1470.
‘Stereoselective Rh2(S-IBAZ)4-Catalyzed Cyclopropanation of Alkenes, Alkynes and Allenes: Asymmetric Synthesis of Diacceptor Cyclopropylphosphonates and Alkylidenecyclopropanes’.

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(7) Lindsay, V. N. G.; Charette, A. B. ACS Catal. 2012, 2, 1221-1225.
‘Design and Synthesis of Chiral Heteroleptic Rhodium(II) Carboxylate Catalysts: Experimental Investigation of Halogen Bond Rigidification Effects in Asymmetric Cyclopropanation’.

(6) Moreau, B.; Alberico, D.; Lindsay, V. N. G.; Charette, A. B. Tetrahedron 2012, 68, 3487-3496.
‘Catalytic Asymmetric Synthesis of Nitrocyclopropane Carboxylates’.

(5) Lindsay, V. N. G.; Nicolas, C.; Charette, A. B. J. Am. Chem. Soc. 2011, 133, 8972-8981.
‘Asymmetric Rh(II)-Catalyzed Cyclopropanation of Alkenes with Diacceptor Diazo Compounds: p-Methoxyphenyl Ketone as a General Stereoselectivity Controlling Group’.

(4) Marcoux, D.; Lindsay, V. N. G.; Charette, A. B. Chem. Commun. 2010, 46, 910-912.
‘Use of achiral additives to increase the stereoselectivity in Rh(II)-catalyzed cyclopropanations’.

(3) Lindsay, V. N. G.; Lin, W.; Charette, A. B. J. Am. Chem. Soc. 2009, 131, 16383-16385.
‘Experimental Evidence for the All-Up Reactive Conformation of Chiral Rhodium(II) Carboxylate Catalysts: Enantioselective Synthesis of cis-Cyclopropane α-Amino Acids’.
Highlighted in Synfacts: Lindsay, V. N. G.; Lin, W.; Charette, A. B. Synfacts 2010, 0198.

undergraduate

(Université de Montréal)

(2) Charette, A. B.; Côté, A.; Desrosiers, J.-N.; Bonnaventure, I.; Lindsay, V. N. G.; Lauzon, C.; Tannous, J.; Boezio, A. A. Pure Appl. Chem. 2008, 80, 881-890.
‘New methods in asymmetric catalysis based on new hemi-labile bidentate ligands’.

(1) Côté, A.; Lindsay, V. N. G.; Charette, A. B. Org. Lett. 2007, 9, 85-87.
‘Application of the Chiral Bis(phosphine) Monoxide Ligand to Catalytic Enantioselective Addition of Dialkylzinc Reagents to β-Nitroalkenes’.
Highlighted in Synfacts: Côté, A.; Lindsay, V. N. G.; Charette, A. B. Synfacts 2007, 0411.

Book Chapters

(4) Lindsay, V. N. G. ‘Rhodium(II)-Catalyzed Cyclopropanation’ (Chapter 15) in Rhodium Catalysis in Organic Synthesis: Methods and Reactions; Wiley-VCH; 2018; pp. 433-448 (Editor: Ken Tanaka).

(3) Charette, A. B.; Lindsay, V. N. G. ‘Stereoselective Formation of Amines by Nucleophilic Addition to Azomethine Derivatives’ in Stereoselective Formation of Amines. Top. Curr. Chem. 2014, 343, 33-74 (Springer, Editors: Wei Li and Xumu Zhang).

(2) Lindsay, V. N. G.; Charette, A. B. ‘Nucleophilic Addition of Non-Stabilized Carbanions to Imines and Imine Derivatives’ (Chapter 1.11) in Comprehensive Organic Synthesis (2nd Edition, Vol. 1), Oxford: Elsevier Science Ltd.; 2014; pp. 365-394 (Editors: Gary A. Molander and Paul Knochel).

(1) Roy, M.-N.; Lindsay, V. N. G.; Charette, A. B. ‘Cyclopropanation Reactions’ (Chapter 1.14) in Stereoselective Synthesis: Stereoselective Reactions of Carbon-Carbon Double Bonds; Georg Thieme Verlag KG; New York; 2011; pp 731-817 (Editor: Johannes de Vries).

Other contributions

(10) Lindsay, V. N. G. ‘1-(Phenylsulfonyl)cyclopropanol’. Encyclopedia of Reagents for Organic Synthesis, 2024. A. B.
Charette, D. Crich, R. A. Shenvi, G. A. Molander (Eds); John Wiley & Sons Ltd.: Chichester, 2nd Ed.; (I.D.: RN02563,
In press).

(9) Lindsay, V. N. G. ‘Methyl Phenyl Sulfone’ (Update) Encyclopedia of Reagents for Organic Synthesis, 2023. A. B. Charette, D. Crich, P. L. Fuchs, G. A. Molander (Eds); John Wiley & Sons Ltd.: Chichester, 2nd Ed.; (I.D.: RM232.pub2)

(8) Lindsay, V. N. G. ‘Dirhodium(II) Tetrakis[R-2-oxaazetidine-4(S)-carboxylate]’ (Update) Encyclopedia of Reagents for Organic Synthesis, 2017. A. B. Charette, D. Crich, P. L. Fuchs, G. A. Molander (Eds); John Wiley & Sons Ltd.: Chichester, 2nd Ed.; (I.D.: RN00607.pub2)

(7) Lindsay, V. N. G. ‘Methyl α-diazo-4-methoxy-β-oxobenzenepropanoate’ Encyclopedia of Reagents for Organic Synthesis, 2012. A. B. Charette, D. Crich, P. L. Fuchs, G. A. Molander (Eds); John Wiley & Sons Ltd.: Chichester, 2nd Ed.; (I.D.: RN01540).

(6) Lindsay, V. N. G. ‘α-Diazo-4-methoxy-β-oxobenzenepropanenitrile’ Encyclopedia of Reagents for Organic Synthesis, 2012. A. B. Charette, D. Crich, P. L. Fuchs, G. A. Molander (Eds); John Wiley & Sons Ltd.: Chichester, 2nd Ed.; (I.D.: RN01541).

(5) Lindsay, V. N. G. ‘2-Diazo-1-(4-methoxyphenyl)-2-nitroethanone’ Encyclopedia of Reagents for Organic Synthesis, 2012. A. B. Charette, D. Crich, P. L. Fuchs, G. A. Molander (Eds); John Wiley & Sons Ltd.: Chichester, 2nd Ed.; (I.D.: RN01542).

(4) Lindsay, V. N. G. ‘2-Azido-1,3-dimethylimidazolinium Chloride’ Encyclopedia of Reagents for Organic Synthesis, 2011. A. B. Charette, D. Crich, P. L. Fuchs, G. A. Molander (Eds); John Wiley & Sons Ltd.: Chichester, 2nd Ed.; (I.D.: RN01465).

(3) Lindsay, V. N. G. ‘1-Nitropropane’ (Update) Encyclopedia of Reagents for Organic Synthesis, 2011. A. B. Charette, D. Crich, P. L. Fuchs, G. A. Molander (Eds); John Wiley & Sons Ltd.: Chichester, 2nd Ed.; (I.D.: RN051).

(2) Lindsay, V. N. G. ‘Nitromethane’ (Update) Encyclopedia of Reagents for Organic Synthesis, 2011. A. B. Charette, D. Crich, P. L. Fuchs, G. A. Molander (Eds); John Wiley & Sons Ltd.: Chichester, 2nd Ed.; (I.D.: RN041).

(1) Lindsay, V. N. G. ‘Dirhodium(II) Tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate]’ Encyclopedia of Reagents for Organic Synthesis, 2010. A. B. Charette, D. Crich, P. L. Fuchs, G. A. Molander (Eds); John Wiley & Sons Ltd.: Chichester, 2nd Ed.; (I.D.: RN01265).

‡ Indicates equal contribution

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