Kara Bren
University of Rochester, NY·Chemistry
Chemists who want to make new medicines or materials are limited by the molecular shapes they can build and by how many steps it takes to build them. Two awards support work on reactions that quickly assemble unusual molecular frameworks using two underexplored reactive intermediates: N-alkenylnitrones and N,O-dialkenylhydroxylamines.
- Fields
Chemistry
- Topics
N-alkenylnitrones
N,O-dialkenylhydroxylamines
azetidines
- Grants
- 2 known grants, through Jul 2028
What they work on
- Develop torquoselective and catalytic asymmetric 4-pi and 6-pi electrocyclizations of N-alkenylnitrones, where the direction of ring closure sets handedness, to make enantioenriched azetidine nitrones and oxazines.
- Carry out diastereoselective functionalizations of azetidine nitrones, strained four-membered nitrogen rings, to build structurally diverse products with defined three-dimensional shapes.
- Determine how attached substituents control the sigmatropic rearrangements of N-alkenylisoxazolines, and develop catalytic asymmetric versions that yield enantioenriched 1-pyrrolines.
- Generate N,O-dialkenylhydroxylamines by metal-catalyzed addition to alkynes and convert them, through nitrone-templated sigmatropic rearrangements and C–H bond insertion, into 1,4-dicarbonyl compounds.
- Supply the architecturally diverse products of these reactions to medicinal and agrichemical compound libraries for biological activity testing.
More about the research
Both are short-lived building blocks, nicknamed "synthons" or linchpins, that can rearrange into more stable products with well-defined three-dimensional shapes. The goal is both practical, expanding the range of accessible molecules, and fundamental, explaining how these intermediates react.
Why it matters
Faster, more selective routes to molecular architectures that are currently hard to make could help chemists discover and study biologically active compounds; products from this work are being placed in medicinal and agrichemical screening libraries. The same reactivity could support the development of new materials, and a clearer mechanistic picture of these intermediates adds to the general synthetic toolbox.
Known grants
From NIH and NSF research grants. Labs often have other funding we can't see.
Closest labs
Brian Stoltz
California Institute of Technology, CA·Chemistry
Develop new stereoselective reactions that produce densely substituted, enantioenriched building blocks for synthesizing complex molecules.
Ming Chen
Virginia Polytechnic Institute and State University, VA·Chemistry·Early-career
Develop asymmetric transformations of 1,1-bisborylalkanes bearing two chemically distinct boron groups on one carbon, so that each group can be activated separately to attach fragments in a chosen order.
Ramesh Giri
Pennsylvania State University, PA·Chemistry
Develop transition-metal-catalyzed difunctionalization of alkenes bearing simple functional groups, using a dual ligand system of electron-deficient alkenes and organic nitriles to stabilize intermediates and promote C(sp3)–C(sp3) bond formation.
The school
University of Rochester: 38 labs on PI Pages, $492M a year on research, 308 research doctorates a year.
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