The W Lab, Spring Graduation 2019
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The W Lab @ TempleOur lab aims to develop a multifaceted research program that leverages a unique class of hypervalent iodine reagents in novel approaches to "umpolung" or reverse-polarity chemistry, Our research encompasses reagent development, new synthetic methods, and the application of these tools to the synthesis of natural products containing challenging medium-ring heterocycles. We aim to bridge the gap between the three-dimensional molecular complexity of nature and the planar aromatic structures of small molecule libraries by introducing simplified strategies and novel disconnections of these valuable architectures.
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W Lab News
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The Wengryniuk Lab has been awarded an NSF CAREER award!!! This award will support our adventures in the total synthesis of medium-ring ether natural products and umpolung C–H activation strategies. We are also so excited to launch some amazing outreach programs to mentor young women in science.
Thank you to the NSF for your support! |
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Breaking News and Events
August 19, 2019: Xiao and Nate's paper entitled "Dearomatization of Electron-Deficient Phenols to ortho-Quinones Enabled by Bidentate Nitrogen-Ligated I(V) Reagents" has been accepted for publication in Angewandte Chemie: DOI: 10.1002/anie.201909868.
This work provides the first general synthetic method for the oxidation of electron-deficient phenols, substrates that have remained elusive as they are inert to common oxidants. The resulting ortho-quinones represent valuable synthetic building blocks for complex molecule synthesis and we showcase several methods for their one-pot derivatization. Building from our lab's work with I(III) N-HVIs, this work relies on a class of bidentate nitrogen-ligated I(V) reagents, or Bi(N)-HVIs, and represents their first synthetic application. Beyond the enhanced reactivity of these Bi(N)HVIs, the presence of a bidentate nitrogen ligand results in a much more tunable platform for the design and development of I(V) reagents which our laboratory is continuing to pursue! Stay tuned!!
This work provides the first general synthetic method for the oxidation of electron-deficient phenols, substrates that have remained elusive as they are inert to common oxidants. The resulting ortho-quinones represent valuable synthetic building blocks for complex molecule synthesis and we showcase several methods for their one-pot derivatization. Building from our lab's work with I(III) N-HVIs, this work relies on a class of bidentate nitrogen-ligated I(V) reagents, or Bi(N)-HVIs, and represents their first synthetic application. Beyond the enhanced reactivity of these Bi(N)HVIs, the presence of a bidentate nitrogen ligand results in a much more tunable platform for the design and development of I(V) reagents which our laboratory is continuing to pursue! Stay tuned!!
July 17, 2019: Myriam and Sophie's paper entitled "Chemoselective Oxidation of Equatorial Alcohols with N-Ligated Lambda-3 Iodanes" has been accepted for publication in Organic Letters: https://doi.org/10.1021/acs.orglett.9b02018)!
This work fills a remaining gap in the selective functionalization of complex scaffolds: the chemoselective oxidation of equatorial over axial alcohols! Using two mild, operationally simple procedures, the simple pyridine ligated N-HVI "Py-HVI" enables the general oxidation of alcohols to ketones with an I(III)-reagent, which offers safety and practical advantages over typical I(V) and Cr(VI) oxidants. The conformational selectivity is explored in detail and a model for predicting the relative rates of oxidation is provided. We hope that this protocol provides a new tool for complex molecule total synthesis! Congrats to Myriam and Sophie on some great work!
This work fills a remaining gap in the selective functionalization of complex scaffolds: the chemoselective oxidation of equatorial over axial alcohols! Using two mild, operationally simple procedures, the simple pyridine ligated N-HVI "Py-HVI" enables the general oxidation of alcohols to ketones with an I(III)-reagent, which offers safety and practical advantages over typical I(V) and Cr(VI) oxidants. The conformational selectivity is explored in detail and a model for predicting the relative rates of oxidation is provided. We hope that this protocol provides a new tool for complex molecule total synthesis! Congrats to Myriam and Sophie on some great work!
