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4 results on '"Bradley T. Reid"'

1. Stereoselective Synthesis of Cyclic Guanidines by Directed Diamination of Unactivated Alkenes

Author

Kyle Young, Armen Zakarian, Bradley T. Reid, Artur K. Mailyan, and Joanna L. Chen

Subjects
Reaction conditions, Molecular Structure, 010405 organic chemistry, Organic Chemistry, Stereoisomerism, Alkenes, 010402 general chemistry, Guanidines, 01 natural sciences, Biochemistry, Article, 0104 chemical sciences, chemistry.chemical_compound, Acetic acid, chemistry, Functional group, Organic chemistry, Stereoselectivity, Physical and Theoretical Chemistry, Guanidine, Amination
Abstract

A method for a directed stereoselective guanidinylation of alkenes is described. The guanidine unit can be delivered as an intact fragment by a hydroxy or carboxy group, usually with a high level of stereocontrol. After the guanidine delivery, the directing group can be cleaved under exceptionally mild conditions, typically by alcoholysis in the presence of acetic acid. Broad functional group tolerance and mild reaction conditions for the cycloguanidilation suggest applications in medicinal chemistry and natural products synthesis.

Published
2016
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2. Total Synthesis of (+)-Guadinomic Acid via Hydroxyl-Directed Guanidylation

Author

Artur K. Mailyan, Armen Zakarian, and Bradley T. Reid

Subjects
Natural product, 010405 organic chemistry, Extramural, Hydroxyl Radical, Organic Chemistry, Total synthesis, Stereoisomerism, Chemistry Techniques, Synthetic, 010402 general chemistry, Imidazolidines, 01 natural sciences, Combinatorial chemistry, Catalysis, Article, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Guadinomic acid, Stereoselectivity, Guanidine, Caproates
Abstract

Protecting-group-free total synthesis of (+)-guadinomic acid is reported using δ-valerolactone as a readily available starting material. The protocol utilizes the recent hydroxyl-directed guanidylation of unactivated alkenes as an approach for direct stereoselective incorporation of the guanidine unit furnishing the natural product in 7 steps.

Published
2018

3. Improved methods for evaluating the environmental impact of nanoparticle synthesis†

Author

Bradley T. Reid and Scott M. Reed

Subjects
Computer science, Nanoparticle, Nanotechnology, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Pollution, Article, 0104 chemical sciences, Colloidal gold, Environmental Chemistry, Green chemistry metrics, 0210 nano-technology
Abstract

With the market for products containing nanoparticles growing, improvements in the efficiency of nanoparticle synthesis are poised to have significant positive economic and environmental impacts. While many metrics have been designed for measuring the efficiency of small molecule synthesis, the use of these metrics for evaluating nanoparticle preparation has not been optimized. Here, a critical evaluation of various green chemistry metrics is provided as they are applied to a common set of nanoparticle synthetic methods. The effect of the nanoparticle polydispersity on the relative greenness of different synthetic methods is also examined. Using metrics modified to account for polydispersity, a case study of gold nanoparticle syntheses is provided and three different methods of preparing monodisperse gold nanoparticles are compared. Interestingly, not all of the metrics provide the same rankings for the synthetic methods. And when polydispersity is ignored, the metrics provide a different rank order of the methods, highlighting the importance of clearly defining the desired nanoparticle size range to avoid underestimating the environmental impact.

Published
2017

4. 2024 Medicinal Chemistry Reviews

Author

Thomas A. Baillie, Andrew G. Capacci, Nick A. Paras, Karin Worm, James L. Carr, Mia C. Callens, Ethan Chidlow, Tryfon Zarganes-Tzitzikas, Katherine S. England, Paul E. Brennan, Yonghong Song, Nicholas Wurtz, Kevin J. Filipski, Kentaro Futatsugi, Robert Dullea, Michelle R. Garnsey, Daniel J. Smaltz, Matthew M. Weiss, Jack A. Terrett, Huifen Chen, Marion Lanier, Samantha Evans, Gregory Williams, Joshua Wollam, Debra Brennan, Yufan Liang, Scott Mlynarski, Bing-Yan Zhu, David J. St. Jean, Trang Tieu, Angel Guzman-Perez, Alexander M. Taylor, Linjie Li, Chenxi Wang, Liuzhi Hu, Xiaowu Dong, Jinxin Che, Andrew S. Bell, James A. Brannigan, Kevin X. Rodriguez, Isaac D. Falk, Bradley T. Reid, Greta Klejborowska, Camilla Scarpellini, Caroline Lanthier, Koen Augustyns, Benjamin D. Sellers, Brian R. Hearn, Katerina Leftheris*, Jennifer X. Qiao, Abdellatif El Marrouni, Abbas Walji, Matthew A. Marx, Jill Hallin, James Christensen, Brad Fell, David W. Lin, Megan Armstrong, Jennifer Jiang, Juan del Pozo, Christiana N. Teijaro, Erika Araujo, Björn Bartels, Ian M. Be, Thomas A. Baillie, Andrew G. Capacci, Nick A. Paras, Karin Worm, James L. Carr, Mia C. Callens, Ethan Chidlow, Tryfon Zarganes-Tzitzikas, Katherine S. England, Paul E. Brennan, Yonghong Song, Nicholas Wurtz, Kevin J. Filipski, Kentaro Futatsugi, Robert Dullea, Michelle R. Garnsey, Daniel J. Smaltz, Matthew M. Weiss, Jack A. Terrett, Huifen Chen, Marion Lanier, Samantha Evans, Gregory Williams, Joshua Wollam, Debra Brennan, Yufan Liang, Scott Mlynarski, Bing-Yan Zhu, David J. St. Jean, Trang Tieu, Angel Guzman-Perez, Alexander M. Taylor, Linjie Li, Chenxi Wang, Liuzhi Hu, Xiaowu Dong, Jinxin Che, Andrew S. Bell, James A. Brannigan, Kevin X. Rodriguez, Isaac D. Falk, Bradley T. Reid, Greta Klejborowska, Camilla Scarpellini, Caroline Lanthier, Koen Augustyns, Benjamin D. Sellers, Brian R. Hearn, Katerina Leftheris*, Jennifer X. Qiao, Abdellatif El Marrouni, Abbas Walji, Matthew A. Marx, Jill Hallin, James Christensen, Brad Fell, David W. Lin, Megan Armstrong, Jennifer Jiang, Juan del Pozo, Christiana N. Teijaro, Erika Araujo, Björn Bartels, and Ian M. Be

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