Another day another preprint on ChemRxiv! “Leveraging Atropisomerism to Obtain a Mutant-Selective c-KIT Inhibitor in Gastrointestinal Stromal Tumors” A story of privileged heterocycles, atropisomerism and kinase selectivity. chemrxiv.org/doi/full/10....

Excited to share our new ChemRxiv preprint: “Leveraging Conformational Control of Neratinib’s C–N Axes to Enhance HER4 Selectivity in Ovarian Cancer” Read here: doi.org/10.26434/che...

had to skip today's morning sessions at ACS to get to airport the suggested 5 hours early..., and got through security in under 5 minutes....

The final version of this manuscript is up at acs catalysis. pubs.acs.org/doi/10.1021/...

A Rh(II)-Catalyzed Atropisomer Selective Ring Expansion of 3-Aryl Indoles to 4-Aryl Quinolines

Heterocycles containing stereogenic axes are becoming increasingly important throughout the drug discovery endeavor, and methodologies that provide access to pharmaceutically relevant atropisomers are in high demand. Herein, we report the rhodium(II)-catalyzed atropisomer selective ring expansion of 3-aryl indoles with α-halodiazoacetates to furnish 4-aryl quinolines in good yields and enantioselectivity, with strong correlations between enantioselectivity and steric bulk observed at different positions of the substrate. Computational studies suggest that the chemistry proceeds via a Dynamic Kinetic Resolution (DKR) process wherein the catalyst reacts preferentially with the Ra conformation of the rapidly racemizing 3-aryl indole starting material to give a cyclopropanated indoline intermediate that undergoes a Ciamician–Dennstedt-type ring expansion before the intermediate’s prospective stereogenic axis can epimerize. The utility of this skeletal transformation is further demonstrated by the derivatization of enantioenriched products, granting access to a structurally diverse array of enantioenriched quinolines.

pubs.acs.org

Gustafson Group@gustafsonlabsbu.bsky.social · last yr.

I have been fairly quiet on Bluesky, but I figured I would break the silence to share this preprint from my group. Inspired by all the great recent skeletal editing work, we developed an atropisomer selective strategy to take Indoles to quinolines. chemrxiv.org/engage/chemr...

Reposting this. about one more week to the deadline!

Gustafson Group@gustafsonlabsbu.bsky.social · 10mo ago

The Stony Brook Chemistry Department is searching for a Chemical Biologist at the Associate or Full professor Level. Come join us on Long Island and do some great science! apply.interfolio.com/174211

Check out our 2nd preprint of the week! It was a privilege to collaborate with @gustafsonlabsbu.bsky.social to demonstrate that our recently developed radical photocages enable quick and simple photo-induced trifluoromethylation of small molecule organics and API's. chemrxiv.org/engage/chemr...

Facile Trifluoromethylation of Arenes and Heterocycles via a Bench Stable Photocaged Trifluoromethylation Reagent

Herein we report a simple radical aromatic trifluoromethylation process that utilizes a cationic, aromatic sulfonate ester as a trifluoromethyl radical photocage. This chemistry allows for the rapid a...

chemrxiv.org

Check out our latests work in collaboration with @taylorlab-chembio.bsky.social! We evaluated their biomolecular photocaged trifluormethylation reagent on small molecules, finding it effected rapid trifluoromethylation of diverse aromatics, including several APIs. chemrxiv.org/engage/chemr...

The Stony Brook Chemistry Department is searching for a Chemical Biologist at the Associate or Full professor Level. Come join us on Long Island and do some great science! apply.interfolio.com/174211

Less than a decade ago, reactions for adding, deleting, and swapping single atoms in complex organic molecules were almost unheard of. Now there’s a growing community of researchers working on them. cen.acs.org/synthesis/Sk... #chemsky 🧪

Skeletal editing: How close are we to true cut-and-paste chemistry?

Reactions that alter organic scaffolds by a single atom are already proving useful, but time will tell if they’ll fundamentally change how molecules are made

cen.acs.org

Great paper here on @chemrxiv.bsky.social from the Lipschultz lab @jeflip.bsky.social - 1st author J. Shah just gave a super talk on this Ti-cat dehydroxylation work at our ACS Conn. Valley Section symposium today - really neat rearrangements and compound fragmentations as synthetic strategy too

Degradative Alcohol Functionalization by Titanocene Photocatalysis

Organotitanium complexes are scarcely employed in photocatalytic reactions despite their robust ligand-to-metal charge-transfer photo-chemistry. Herein, we describe the development of titanocene pho-t...

chemrxiv.org

Just got back from another excellent Heterocyclic Compounds GRC and am excited to have been elected Vice-Chair. I look forward to putting together an exciting program in 2027! Happy to hear any cool ideas for session topics.

Really excited to share this work. Lots of fun and opportunities with Cp-ligated Ti complexes. Especially proud of Jagrut for spearheading our efforts when he transferred into the group in summer 2023.

Lipshultz Group@lipshultzsbu.bsky.social · last yr.

Sharing our 1st preprint on our work on organo-Ti photocatalysis! We've found that titanocenes are photoactive catalysts for alcohol activation by LMCT excitation, enabling β-scission of alkoxyl radicals for degradative functionalization. Congrats Jagrut, Ashley & the whole team!

This week marked the 3rd SBU-BNL Photochemistry Supergroup, with a great poster session and 10 speakers from @stonybrooku.bsky.social Chemistry & MSCE, @brookhavenlab.bsky.social @queenscollegecuny.bsky.social, @hofstrau.bsky.social, and @adelphiu.bsky.social! Thanks to SBU ORI for support!

I'm excited to share that I'll be joining the Chemistry Department at Stony Brook University as a tenure-track Assistant Professor this fall! My group will use fundamental organic transformations to advance polymeric biomaterials. Check out jillalty.com for more information.

We are looking for a new postdoc to join @lipshultzsbu.bsky.social to work on synthetic methods enabled by catalytic photochemistry of catalyst-substrate complexes! Please apply here by May 8: stonybrooku.taleo.net/careersectio... #chempostdoc

Great news: NIH postbac program is recruiting again! If your grad school plans were affected by program cutbacks or admissions freezes this year I highly encourage you to apply, this could be a perfect opportunity. Please repost. www.training.nih.gov/research-tra...

Asymmetric Carbon Insertion!

Gustafson Group@gustafsonlabsbu.bsky.social · last yr.

I have been fairly quiet on Bluesky, but I figured I would break the silence to share this preprint from my group. Inspired by all the great recent skeletal editing work, we developed an atropisomer selective strategy to take Indoles to quinolines. chemrxiv.org/engage/chemr...

I have been fairly quiet on Bluesky, but I figured I would break the silence to share this preprint from my group. Inspired by all the great recent skeletal editing work, we developed an atropisomer selective strategy to take Indoles to quinolines. chemrxiv.org/engage/chemr...

New report shows that NIH grants fueled $95 billion in economic activity and 407,782 jobs in 2024. That's not to mention the countless lives that biomedical research has saved. Show me a better investment than that. www.forbes.com/sites/michae...

NIH Grants Fueled $95 Billion In FY 2024 Economic Activity, Finds New Report

National Institutes of Health grants generated almost $95 billion in economic activity nationwide in FY 2024 according to a new report by United for Medical Research.

forbes.com

🎉 A new way to celebrate in the Lipshultz Group! Our first paper warrants a sweet treat, and we've decided to make it a tradition. Here's to many more paper cakes! 🎂

I guess it's time for an actual post. Celebrating the end of my first semester at Stony Brook with post doc @grustin.bsky.social and a talented group of rotation students at the aptly named (but not chemistry themed) The Bench

First post and I’m excited to connect with #chemsky! My group has a broad interest in molecular inorganic and organometallic #chemistry with a focus on developing new platforms for controlling the selectivity of (electro)catalytic reactions. We also have an open postdoc position, see 👇 for info!