Seminars Archive

Stereoselective Synthesis and Applications of Sulfonylcyclopropanols as Modular Cyclopropanone and Homoenolate Equivalents

Dr. Vincent Lindsay | North Carolina State University |

Professor Mike Hilinski

Cyclopropanone derivatives have long been regarded as unusable and elusive synthetic intermediates, mainly owing to their prominent ring strain and kinetic instability. In this work, we report the enantioselective synthesis of sulfonylcyclopropanols, shown to be modular and versatile
synthetic equivalents of the corresponding cyclopropanone derivatives. These reagents were found to smoothly react in a variety of reaction manifolds, including organometallic 1,2-addition affording cyclopropanols, nitrene chemistry to access chiral β-lactams, nickel-catalyzed C–C
activation to cyclopentenones, as well as olefination chemistry as a general platform to chiral alkylidenecyclopropanes and other substituted cyclopropanes. Moreover, we have shown that these sulfonylcyclopropanols can also behave as ‘electrophilic homoenolate’ equivalents,
effectively acting as ring-opened 2- or 3-carbon linchpin reagents depending on the reaction conditions. This work constitutes the first general enantioselective route to cyclopropanone equivalents, thus unlocking a number of novel synthetic disconnections relevant to a variety of
chemical industries.

Dr. Huiyuan Zhu | Virginia Tech

Professor Jill Venton

Dr. Leah Dodson | University of Maryland, College Park

Professor Eric Herbst

Dr. Christina Cooley | Trinity University

Professor Mike Hilinski

Dr. Robert Gilliard | University of Virginia

Professor Jill Venton

Dr. Javier Grajeda | Eastman

Professor Brent Gunnoe

Dr. Ryan Fortenberry | University of Mississippi

Professor Robin Garrod

Dr. Charles Machan | University of Virginia

Professor Dean Harman

Special Seminar

Tuning the Reactivity Landscape of Metalloenzymes: From Active Site Modifications to Long-range Dynamic Effects | Dr. Paulo Zaragoza |University of California, Berkeley

UVA Rising Star in Chemistry Postdoctoral Seminar series

Join Zoom Meeting
https://virginia.zoom.us/j/91919004812?pwd=R0lGUGsvM2I4Y3dSVU85Nm9tQ0VXUT09

Meeting ID: 919 1900 4812
Passcode: 290863

Special Seminar

Modulation of MALT1 pre-mRNA structure by hnRNP proteins regulates T-cell activation | Dr. Alisha (Jonesy) Jones | Helmholtz Zentrum München, Munich, Germany

UVA Rising Star in Chemistry Postdoctoral Seminar series

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https://virginia.zoom.us/j/98531118370?pwd=dUVJd1Ria2QzdzR2MjZkcjJkM2pyUT09

Meeting ID: 985 3111 8370 Passcode: 103820

Challenges and Opportunities in Chemical Separations with Porous Materials

Dr. Michael Katz | Memorial University of Newfoundland |

Diane Dickie, Ph.D., Senior Scientist

Challenges and Opportunities in Chemical Separations with Porous Materials

Porous materials such as metal-organic frameworks have been extensively studied for applications in gas-adsorption, catalysis, and chemical separation (to name a few). With particular focus on separations, one of the long-term goals in my research program is to implement porous materials in real-world applications. For the research team to be successful, it is critical to address these challenges from a top-down approach. Factoring in issues such as partial pressure, overall gas composition, and regeneration need be at the forefront of the research. With that in mind, the presentation will explore how porous materials can be designed to address the challenges associated with chemical separations.

Dr. Robert Kennedy | University of Michigan

Professors Rebecca Pompano and Jill Venton

The Nanoliter Lab: Droplet Microfluidics for Screening and Sensing

Manipulating samples as droplets within microfluidic devices has emerged as an interesting approach for chemical analysis and screening. In segmented flow, one embodiment of this technology, nanoliter samples are manipulated in microfluidic channels as plugs separated by an immiscible fluid, such as air or fluorinated oil. These plugs serve as miniature test-tubes in which reactions can be performed at high throughput. Microfluidic tools have been developed to split, dilute, extract, and filter such plugs at rates >10 samples/s. We have developed methods to analyze plug content by electrophoresis and mass spectrometry (MS). A natural application of this technology is for high throughput screening. By coupling droplet manipulation with MS detection, it is possible to greatly reduce reagent consumption and eliminate the need for fluorescent labels or coupled reactions. The technology and application to screens of deacetylase reactions and protein-protein interactions will be presented. A more involved screening allows for monitoring reactions of enzyme variants to identify new biocatalysts. Droplet technology can also be used for chemical monitoring or sensing applications. In this approach samples emerging from a miniaturized sampling device are segmented for later analysis. We have used this method to monitor neurotransmitter dynamics in the brain. The technology and application to studies of neurotransmission in a Huntington’s disease models will be demonstrated.