Welcome to the Gold Lab at UNM
Understanding bioorganic structure and reactivity for the precise control of molecular properties and transformations


* Indicates equal author contributions

23. Windsor, I. W.; Gold, B.; Raines, R. T. An n➝π* Interaction in the Bound Substrate of Aspartic Proteases Replicates the Oxyanion Hole. ACS Catalysis, 2019, 9, 1464.

22. Windsor, I. W.; Palte, M. J.; Lukesh, J. C., III; Gold, B.; Forest, K. T.; Raines, R. T. Sub-picomolar Inhibition of HIV-1 Protease with a Boronic Acid. J. Am. Chem. Soc. 2018, 140, 14015.

21. Burke, E. G.;* Gold, B.;* Hoang, T. T.; Raines, R. T.; Schomaker, J. M. Fine-Tuning Strain and Electronic Activation of Strain-Promoted 1,3-Dipolar Cycloadditions with Endocyclic Sulfamates in SNO-OCTS. J. Am. Chem. Soc. 2017, 139, 8029.

20. Alabugin, I. V.; Gold, B. Stereoelectronic Effects: Origins and Consequences on Structure and Reactivity of Organic Molecules. in: Wang, Z. Encyclopedia of Physical Organic Chemistry; Wiley: Chichester, 2017.

19. Chyan, W.; Kilgore, H. R.; Gold, B.; Raines, R. T. Electronic and Steric Optimization of Simple Fluorogenic Probes for Biomolecular Imaging. J. Org. Chem. 2017, 82, 4297.

18. Gold, B.;* Aronoff, M. R.;* Raines, R. T. 1,3-Dipolar Cycloadditions with Diazo Groups: Noncovalent Interactions Overwhelm Strain. Org. Lett. 2016, 18, 4466.         

17. Gold, B.;* Aronoff, M. R.;* Raines, R. T. Decreasing Distortion Energies without Strain: Diazo-Selective 1,3-Dipolar Cycloadditions. J. Org. Chem. 2016, 81, 5998.

16. Aronoff, M. R.;* Gold, B.;* Raines, R. T. 1,3-Dipolar Cycloadditions of Diazo Compounds in the Presence of Azides. Org. Lett. 2016, 18, 1538.       

15. Aronoff, M. R.;* Gold, B.;* Raines, R. T. Rapid Cycloaddition of a Diazo Group with an Unstrained Dipolarophile. Tetrahedron Lett. 2016, 57, 2347.                       

14. Mohamed, R. K.;* Mondal, S.;* Gold, B.; Evoniuk, C. J.; Banerjee, T.; Hanson, K.; Alabugin, I. V. Alkenes as Alkyne Equivalents in Radical Cascades Terminated by Fragmentations: Overcoming Stereoelectronic Restrictions on Ring Expansion for the Preparation of Expanded Polyaromatics. J. Am. Chem. Soc. 2015, 137, 6335.

13. Gold, B.; Batsomboon, P.; Dudley, G. B.; Alabugin, I. V. Alkynyl Crown Ethers as a Scaffold for Hyperconjugative Assistance in Non-catalyzed Azide-Alkyne Click Reactions: Ion Sensing through Enhanced Transition State Stabilization. J. Org. Chem. 2014, 79, 6221.

12. Mondal, S.;* Gold, B.;* Mohamed, R. K.; Alabugin, I. V. Design of Leaving Groups in Radical C–C Fragmentations: Through-Bond 2c–3e Interactions in Self-Terminating Radical Cascades. Chem. Eur. J. 2014, 20, 8664.

11. Mondal, S.; Gold, B.; Mohamed, R. K.; Phan, H.; Alabugin, I. V. Rerouting Radical Cascades: Intercepting the Homoallyl Ring Expansion in Enyne Cyclizations via C–S Scission. J. Org. Chem. 2014, 79, 7491.

10. Gold, B.; Dudley, G. B.; Alabugin, I. V. Moderating Strain without Sacrificing Reactivity: Design of Fast and Tunable Non-Catalyzed Alkyne–Azide Cycloadditions via Stereoelectronically Controlled Transition State Stabilization. J. Am. Chem. Soc. 2013, 135, 1558.

9.   Alabugin, I. V.; Gold, B. Two Functional Groups in One Package: Cascade Transformations of Alkynes. J. Org. Chem.—Synopsis, 2013, 78, 7777.

8.   Baranov, D. S.; Gold, B.; Vasilevsky, S. F.; Alabugin, I. V. Divergent Cyclizations of 1-R-Ethynyl-9,10-anthraquinones:  Use of Thiourea as a “S2-” Equivalent in an “Anchor-Relay” Addition Mediated by Formal C–H Activation. J. Org. Chem. 2013, 78, 2074.

7.   Gilmore, K.; Gold, B.; Clark, R. J.; Alabugin, I. V. Convenient, Ambient Temperature Generation of Sulfonyl Radicals. Aust. J. Chem. 2013, 66, 336.

6.   Gold, B.; Shevchenko, N. E.; Bonus, N.; Dudley, G. B.; Alabugin, I. V. Selective Transition State Stabilization via Hyperconjugative and Conjugative Assistance: Stereoelectronic Concept for Copper-Free Click Chemistry. J. Org. Chem. 2012, 77, 75. Nominee for Outstanding Publication of the Year

5.   Batsomboon, P.; Gold, B.; Alabugin, I. V.;  Dudley, G. B. Tandem Nucleophilic Addition/Fragmentation of Vinylogous Acyl Nonaflates for the Synthesis of Functionalized Alkynes, with a Key Mechanistic Insight. Synthesis, 2012, 44, 1818.

4.   Vasilevsky, S. F.; Gold, B.; Mikhailovskaya, T. F.; Alabugin, I. V. Strain Control in Nucleophilic Cyclizations: Reversal of exo-Selectivity in Cyclizations of Hydrazides of Acetylenyl Carboxylic Acids by Annealing to a Pyrazole Scaffold. J. Phys. Org. Chem. 2012, 25, 998.

3.   Baranov, D. S.; Vasilevsky, S. F.; Gold, B.; Alabugin, I. V. Urea as a Solvent and Reagent for the Addition/Cyclization/Fragmentation Cascades Leading to 2-R-7H-dibenzo[de,h]quinolin-7-one Analogues of Aporphinoid Alkaloids. RSC Adv. 2011, 1, 1745.

2.   Stepanov, A. A.; Gornostaev, L. M.; Vasilevsky, S. F.; Arnold, E. V.; Mamatyuk, V. I.; Fadeev, D. S.; Gold, B.; Alabugin, I. V. Chameleonic Reactivity of Vicinal Diazonium Salt of Acetylenyl-9,10- Anthraquinones: Synthetic Application Towards Two Heterocyclic Targets. J. Org. Chem. 2011, 76, 8737.

1.   Alabugin, I. V.; Gold, B.; Shatruk, M.; Kovnir, K. On the “Single-Crystal X-ray Structure of 1,3- Dimethylcyclobutadiene by Confinement in a Crystalline Matrix.” Science, 2010, 330, 1047.
Highlighted in: “Cyclobutadiene ControversyC&EN, 2010, 88(47), 27, and “Debating CyclobutadieneNature Chemistry – The Sceptical Chymist, 2010.