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The Lindsay LAB

PUBLICATIONS

Lindsay Lab

(NC State University)

(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

(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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