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Items: 1 to 50 of 110

2.

Peroxycarbenium Ions as the "Gatekeepers" in Reaction Design: Assistance from Inverse Alpha-Effect in Three-Component β-Alkoxy-β-peroxylactones Synthesis.

Vil' VA, Barsegyan YA, Barsukov DV, Korlyukov AA, Alabugin IV, Terent'ev AO.

Chemistry. 2019 Sep 5. doi: 10.1002/chem.201903752. [Epub ahead of print]

PMID:
31487079
3.

Making endo-cyclizations favorable again: a conceptually new synthetic approach to benzotriazoles via azide group directed lithiation/cyclization of 2-azidoaryl bromides.

Ageshina AA, Chesnokov GA, Topchiy MA, Alabugin IV, Nechaev MS, Asachenko AF.

Org Biomol Chem. 2019 May 8;17(18):4523-4534. doi: 10.1039/c9ob00615j.

PMID:
30994147
4.

CO2 or SO2: Should It Stay, or Should It Go?

Dos Passos Gomes G, Wimmer A, Smith JM, König B, Alabugin IV.

J Org Chem. 2019 May 17;84(10):6232-6243. doi: 10.1021/acs.joc.9b00503. Epub 2019 Apr 29.

PMID:
30993995
5.

Alkynes as Synthetic Equivalents of Ketones and Aldehydes: A Hidden Entry into Carbonyl Chemistry.

Alabugin IV, Gonzalez-Rodriguez E, Kawade RK, Stepanov AA, Vasilevsky SF.

Molecules. 2019 Mar 15;24(6). pii: E1036. doi: 10.3390/molecules24061036. Review.

6.

Stereoelectronic Influence of a "Spectator" Propargylic Substituent Can Override Aromaticity Effects in Radical Peri-Cyclizations en Route to Expanded Polyaromatics.

Hughes AM, Dos Passos Gomes G, Alabugin IV.

J Org Chem. 2019 Feb 15;84(4):1853-1862. doi: 10.1021/acs.joc.8b02779. Epub 2019 Feb 4.

PMID:
30701976
7.

Five Roads That Converge at the Cyclic Peroxy-Criegee Intermediates: BF3-Catalyzed Synthesis of β-Hydroperoxy-β-peroxylactones.

Vil' VA, Gomes GDP, Ekimova MV, Lyssenko KA, Syroeshkin MA, Nikishin GI, Alabugin IV, Terent'ev AO.

J Org Chem. 2018 Nov 2;83(21):13427-13445. doi: 10.1021/acs.joc.8b02218. Epub 2018 Oct 23.

PMID:
30351948
8.

Isonitriles as Stereoelectronic Chameleons: The Donor-Acceptor Dichotomy in Radical Additions.

Gomes GDP, Loginova Y, Vatsadze SZ, Alabugin IV.

J Am Chem Soc. 2018 Oct 31;140(43):14272-14288. doi: 10.1021/jacs.8b08513. Epub 2018 Oct 17.

PMID:
30270623
9.

Upconversion of Reductants.

Syroeshkin MA, Kuriakose F, Saverina EA, Timofeeva VA, Egorov MP, Alabugin IV.

Angew Chem Int Ed Engl. 2019 Apr 16;58(17):5532-5550. doi: 10.1002/anie.201807247. Epub 2019 Feb 20. Review.

PMID:
30063285
10.

Alkyne Origami: Folding Oligoalkynes into Polyaromatics.

Alabugin IV, Gonzalez-Rodriguez E.

Acc Chem Res. 2018 May 15;51(5):1206-1219. doi: 10.1021/acs.accounts.8b00026. Epub 2018 Apr 20.

PMID:
29676896
11.

Ozone-Free Synthesis of Ozonides: Assembling Bicyclic Structures from 1,5-Diketones and Hydrogen Peroxide.

Yaremenko IA, Gomes GDP, Radulov PS, Belyakova YY, Vilikotskiy AE, Vil' VA, Korlyukov AA, Nikishin GI, Alabugin IV, Terent'ev AO.

J Org Chem. 2018 Apr 20;83(8):4402-4426. doi: 10.1021/acs.joc.8b00130. Epub 2018 Mar 30.

PMID:
29533620
12.

Radical Alkyne peri-Annulation Reactions for the Synthesis of Functionalized Phenalenes, Benzanthrenes, and Olympicene.

Tsvetkov NP, Gonzalez-Rodriguez E, Hughes A, Dos Passos Gomes G, White FD, Kuriakose F, Alabugin IV.

Angew Chem Int Ed Engl. 2018 Mar 26;57(14):3651-3655. doi: 10.1002/anie.201712783. Epub 2018 Mar 1.

PMID:
29405588
13.

Interrupted Baeyer-Villiger Rearrangement: Building A Stereoelectronic Trap for the Criegee Intermediate.

Vil' VA, Dos Passos Gomes G, Bityukov OV, Lyssenko KA, Nikishin GI, Alabugin IV, Terent'ev AO.

Angew Chem Int Ed Engl. 2018 Mar 19;57(13):3372-3376. doi: 10.1002/anie.201712651. Epub 2018 Feb 23.

PMID:
29385307
14.

Photochemical Activation of Enediyne Warheads: A Potential Tool for Targeted Antitumor Therapy.

Bhattacharya P, Basak A, Campbell A, Alabugin IV.

Mol Pharm. 2018 Mar 5;15(3):768-797. doi: 10.1021/acs.molpharmaceut.7b00911. Epub 2018 Feb 1. Review.

PMID:
29303588
15.

Erratum: Organocatalyzed synthesis of fluorinated poly(aryl thioethers).

Park NH, Gomes GDP, Fevre M, Jones GO, Alabugin IV, Hedrick JL.

Nat Commun. 2017 Nov 13;8(1):1553. doi: 10.1038/s41467-017-01129-8.

16.

Substituent effects on stereoselectivity of dihalocarbene reactions with cyclohexadiene and on the reactivity of bis-dihalocyclopropanes in electrophilic nitrations en route to pyrimidine N-oxides.

Sedenkova KN, Averina EB, Grishin YK, Kolodyazhnaya JV, Rybakov VB, Kuznetsova TS, Hughes A, Gomes GDP, Alabugin IV, Zefirov NS.

Org Biomol Chem. 2017 Nov 15;15(44):9433-9441. doi: 10.1039/c7ob02463k.

PMID:
29095467
17.

Coupling N-H Deprotonation, C-H Activation, and Oxidation: Metal-Free C(sp3)-H Aminations with Unprotected Anilines.

Evoniuk CJ, Gomes GDP, Hill SP, Fujita S, Hanson K, Alabugin IV.

J Am Chem Soc. 2017 Nov 15;139(45):16210-16221. doi: 10.1021/jacs.7b07519. Epub 2017 Oct 31.

PMID:
29037029
18.

Organocatalyzed synthesis of fluorinated poly(aryl thioethers).

Park NH, Gomes GDP, Fevre M, Jones GO, Alabugin IV, Hedrick JL.

Nat Commun. 2017 Aug 1;8(1):166. doi: 10.1038/s41467-017-00186-3. Erratum in: Nat Commun. 2017 Nov 13;8(1):1553.

19.

Stereoelectronic Interactions as a Probe for the Existence of the Intramolecular α-Effect.

Juaristi E, Dos Passos Gomes G, Terent'ev AO, Notario R, Alabugin IV.

J Am Chem Soc. 2017 Aug 9;139(31):10799-10813. doi: 10.1021/jacs.7b05367. Epub 2017 Jul 25.

PMID:
28701041
20.
21.

Stereoelectronic Control in the Ozone-Free Synthesis of Ozonides.

Dos Passos Gomes G, Yaremenko IA, Radulov PS, Novikov RA, Chernyshev VV, Korlyukov AA, Nikishin GI, Alabugin IV, Terent'ev AO.

Angew Chem Int Ed Engl. 2017 Apr 24;56(18):4955-4959. doi: 10.1002/anie.201610699. Epub 2017 Apr 5.

PMID:
28378382
22.

Coupling Radical Homoallylic Expansions with C-C Fragmentations for the Synthesis of Heteroaromatics: Quinolines from Reactions of o-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals.

Evoniuk CJ, Gomes GDP, Ly M, White FD, Alabugin IV.

J Org Chem. 2017 Apr 21;82(8):4265-4278. doi: 10.1021/acs.joc.7b00262. Epub 2017 Apr 3.

PMID:
28357857
23.

Drawing Catalytic Power from Charge Separation: Stereoelectronic and Zwitterionic Assistance in the Au(I)-Catalyzed Bergman Cyclization.

Dos Passos Gomes G, Alabugin IV.

J Am Chem Soc. 2017 Mar 8;139(9):3406-3416. doi: 10.1021/jacs.6b11054. Epub 2017 Feb 22.

PMID:
28187258
24.

Orbital Crossings Activated through Electron Injection: Opening Communication between Orthogonal Orbitals in Anionic C1-C5 Cyclizations of Enediynes.

Peterson PW, Shevchenko N, Breiner B, Manoharan M, Lufti F, Delaune J, Kingsley M, Kovnir K, Alabugin IV.

J Am Chem Soc. 2016 Dec 7;138(48):15617-15628. Epub 2016 Nov 28.

PMID:
27934008
25.

Stereoelectronic Chameleons: The Donor-Acceptor Dichotomy of Functional Groups.

Vatsadze SZ, Loginova YD, Dos Passos Gomes G, Alabugin IV.

Chemistry. 2017 Mar 8;23(14):3225-3245. doi: 10.1002/chem.201603491. Epub 2016 Nov 11. Review.

PMID:
27862399
26.

Alkynes as Linchpins for the Additive Annulation of Biphenyls: Convergent Construction of Functionalized Fused Helicenes.

Mohamed RK, Mondal S, Guerrera JV, Eaton TM, Albrecht-Schmitt TE, Shatruk M, Alabugin IV.

Angew Chem Int Ed Engl. 2016 Sep 19;55(39):12054-8. doi: 10.1002/anie.201606330. Epub 2016 Aug 18.

PMID:
27535022
27.

Combining Traceless Directing Groups with Hybridization Control of Radical Reactivity: From Skipped Enynes to Defect-Free Hexagonal Frameworks.

Pati K, Dos Passos Gomes G, Alabugin IV.

Angew Chem Int Ed Engl. 2016 Sep 12;55(38):11633-7. doi: 10.1002/anie.201605799. Epub 2016 Aug 18.

PMID:
27534837
28.

Optimizing Protonation States for Selective Double-Strand DNA Photocleavage in Hypoxic Tumors: pH-Gated Transitions of Lysine Dipeptides.

Kaya K, Roy S, Nogues JC, Rojas JC, Sokolikj Z, Zorio DA, Alabugin IV.

J Med Chem. 2016 Sep 22;59(18):8634-47. doi: 10.1021/acs.jmedchem.6b01164. Epub 2016 Aug 31.

PMID:
27526786
29.

Domino Fragmentations in Traceless Directing Groups of Radical Cascades: Evidence for the Formation of Alkoxy Radicals via C-O Scission.

Harris T, Gomes Gdos P, Clark RJ, Alabugin IV.

J Org Chem. 2016 Jul 15;81(14):6007-17. doi: 10.1021/acs.joc.6b01052. Epub 2016 Jun 27.

PMID:
27304982
30.

Double C-H amination by consecutive SET oxidations.

Evoniuk CJ, Hill SP, Hanson K, Alabugin IV.

Chem Commun (Camb). 2016 Jun 4;52(44):7138-41. doi: 10.1039/c6cc03106d. Epub 2016 May 12.

PMID:
27170275
31.

Fused Catechol Ethers from Gold(I)-Catalyzed Intramolecular Reaction of Propargyl Ethers with Acetals.

Pati K, Gomes Gdos P, Harris T, Alabugin IV.

Org Lett. 2016 Mar 4;18(5):928-31. doi: 10.1021/acs.orglett.5b03522. Epub 2016 Feb 17.

PMID:
26886747
32.

Gold(I)-Catalyzed Allenyl Cope Rearrangement: Evolution from Asynchronicity to Trappable Intermediates Assisted by Stereoelectronic Switching.

Vidhani DV, Krafft ME, Alabugin IV.

J Am Chem Soc. 2016 Mar 2;138(8):2769-79. doi: 10.1021/jacs.5b12920. Epub 2016 Feb 23.

PMID:
26850567
33.

Stereoelectronic source of the anomalous stability of bis-peroxides.

Gomes GDP, Vil' V, Terent'ev A, Alabugin IV.

Chem Sci. 2015 Dec 1;6(12):6783-6791. doi: 10.1039/c5sc02402a. Epub 2015 Sep 7.

34.

The Missing C1-C5 Cycloaromatization Reaction: Triplet State Antiaromaticity Relief and Self-Terminating Photorelease of Formaldehyde for Synthesis of Fulvenes from Enynes.

Mohamed RK, Mondal S, Jorner K, Delgado TF, Lobodin VV, Ottosson H, Alabugin IV.

J Am Chem Soc. 2015 Dec 16;137(49):15441-50. doi: 10.1021/jacs.5b07448. Epub 2015 Dec 3.

PMID:
26536479
35.

Synthesis of Functionalized Phenanthrenes via Regioselective Oxidative Radical Cyclization.

Pati K, Michas C, Allenger D, Piskun I, Coutros PS, Gomes Gdos P, Alabugin IV.

J Org Chem. 2015 Dec 4;80(23):11706-17. doi: 10.1021/acs.joc.5b01014. Epub 2015 Aug 14.

PMID:
26248062
36.

Coupling cyclizations with fragmentations for the preparation of heteroaromatics: quinolines from o-alkenyl arylisocyanides and boronic acids.

Evoniuk CJ, Ly M, Alabugin IV.

Chem Commun (Camb). 2015 Aug 18;51(64):12831-4. doi: 10.1039/c5cc04391c.

PMID:
26165765
37.

Alkenes as alkyne equivalents in radical cascades terminated by fragmentations: overcoming stereoelectronic restrictions on ring expansions for the preparation of expanded polyaromatics.

Mohamed RK, Mondal S, Gold B, Evoniuk CJ, Banerjee T, Hanson K, Alabugin IV.

J Am Chem Soc. 2015 May 20;137(19):6335-49. doi: 10.1021/jacs.5b02373. Epub 2015 May 6.

PMID:
25906261
38.

Conformational flexibility of fused tetracenedione propellers obtained from one-pot reductive dimerization of acetylenic quinones.

Vasilevsky SF, Baranov DS, Mamatyuk VI, Fadeev DS, Gatilov YV, Stepanov AA, Vasilieva NV, Alabugin IV.

J Org Chem. 2015 Feb 6;80(3):1618-31. doi: 10.1021/jo502543b. Epub 2015 Jan 27.

PMID:
25575160
39.

Opening Enediyne Scissors Wider: pH-Dependent DNA Photocleavage by meta-Diyne Lysine Conjugates.

Kaya K, Johnson M, Alabugin IV.

Photochem Photobiol. 2015 May-Jun;91(3):748-58. doi: 10.1111/php.12412. Epub 2015 Jan 29.

PMID:
25545396
40.

Traceless directing groups in radical cascades: from oligoalkynes to fused helicenes without tethered initiators.

Pati K, dos Passos Gomes G, Harris T, Hughes A, Phan H, Banerjee T, Hanson K, Alabugin IV.

J Am Chem Soc. 2015 Jan 28;137(3):1165-80. doi: 10.1021/ja510563d. Epub 2015 Jan 13.

PMID:
25539142
41.

Rerouting radical cascades: intercepting the homoallyl ring expansion in enyne cyclizations via C-S scission.

Mondal S, Gold B, Mohamed RK, Phan H, Alabugin IV.

J Org Chem. 2014 Aug 15;79(16):7491-501. doi: 10.1021/jo5012043. Epub 2014 Jul 24.

PMID:
25011054
42.

Alkynyl crown ethers as a scaffold for hyperconjugative assistance in noncatalyzed azide-alkyne click reactions: ion sensing through enhanced transition-state stabilization.

Gold B, Batsomboon P, Dudley GB, Alabugin IV.

J Org Chem. 2014 Jul 3;79(13):6221-32. doi: 10.1021/jo500958n. Epub 2014 Jun 20.

PMID:
24927131
43.

Design of leaving groups in radical C-C fragmentations: through-bond 2c-3e interactions in self-terminating radical cascades.

Mondal S, Gold B, Mohamed RK, Alabugin IV.

Chemistry. 2014 Jul 7;20(28):8664-9. doi: 10.1002/chem.201402843. Epub 2014 Jun 4.

PMID:
24898770
44.

Hybridization trends for main group elements and expanding the Bent's rule beyond carbon: more than electronegativity.

Alabugin IV, Bresch S, Manoharan M.

J Phys Chem A. 2014 May 22;118(20):3663-77. doi: 10.1021/jp502472u. Epub 2014 May 8.

PMID:
24773162
46.

Exo-dig radical cascades of skipped enediynes: building a naphthalene moiety within a polycyclic framework.

Pati K, Hughes AM, Phan H, Alabugin IV.

Chemistry. 2014 Jan 7;20(2):390-3. doi: 10.1002/chem.201304092. Epub 2013 Nov 22.

PMID:
24273130
47.

Drawing from a pool of radicals for the design of selective enyne cyclizations.

Mondal S, Mohamed RK, Manoharan M, Phan H, Alabugin IV.

Org Lett. 2013 Nov 15;15(22):5650-3. doi: 10.1021/ol4028072. Epub 2013 Nov 4.

PMID:
24188522
48.

Finding the right path: Baldwin "rules for ring closure" and stereoelectronic control of cyclizations.

Alabugin IV, Gilmore K.

Chem Commun (Camb). 2013 Dec 14;49(96):11246-50. doi: 10.1039/c3cc43872d.

PMID:
24162562
49.

Stereocontrolled synthesis of (E,Z)-dienals via tandem Rh(I)-catalyzed rearrangement of propargyl vinyl ethers.

Vidhani DV, Krafft ME, Alabugin IV.

Org Lett. 2013 Sep 6;15(17):4462-5. doi: 10.1021/ol4019985. Epub 2013 Aug 22.

PMID:
23968534
50.

"Two functional groups in one package": using both alkyne π-bonds in cascade transformations.

Alabugin IV, Gold B.

J Org Chem. 2013 Aug 16;78(16):7777-84. doi: 10.1021/jo401091w. Epub 2013 Jul 17.

PMID:
23829276

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