Atropisomerism in macrocyclic cyclophanes

Macrocyclic cyclophanes provide fertile ground for investigating phenomena resulting from atropisomerism. In 2023, we developed a modular synthesis of a series of metacyclophanes using Pd-catalyzed C-O bond forming macrocyclizations. Having removed the barrier to synthetic access, we are now designing and studying molecules with unique three-dimensional shapes that truly escape from flatland.

Graduate students in the Li group will learn a combination of method development, synthesis, asymmetric catalysis, and where relevant, organometallic chemistry, to understand and solve the problems they are interested in.

Atom swapping 

The Li group is interested in developing new strategies to modify the carbon framework of natural products with the goal of achieving atom-swapping reactions. Our current focus is on transforming readily available heterocycles into their less common heteroatom isosteres that are more challenging to synthesize by other methods.

Group news

• Nov 2025 - Congratulations to our newly minted Ph.Ds, Dr. Shengkai Wei and Dr. Liang-Yu Chen! The contributions from Shengkai, Tian, and Liang-Yu will continue to inspire the group.
• July 2025 - Tian and Quang publish their work on a C-to-B atom swap on coumarins and dibenzolactones. A big week for Tian!
• July 2025 - Tian successfully defends his thesis! Congrats, Dr. You!
• June 2025 - Shengkai and Liang-Yu's study of atropdiastereomers in macrocyclic metacyclophanes is published! These fascinating macrocycles were designed by Shengkai.
• Dec 2024 - Liang-Yu, Udayan, and Shengkai publish their computational and experimental studies on syn/anti conformational isomerism in metacyclophanes.
• Apr 2024 - Liang-Yu is awarded the David N. and Minnie I. Wall Graduate Fellowship. Well-deserved!
• Apr 2024 - Udayan receives the Edward V. Sayre Chemistry Scholarship. Congratulations!
• Apr 2024 - Shengkai becomes a member of ISU's Chapter of Sigma Xi!
• July 2023 - Liang-Yu's work on skeletal editing by decarboxylation is online.
• May 2023 - Shengkai's and Liang-Yu's paper on the catalytic enantioselective synthesis of planar chiral metacyclophanes is published!
• May 2023 - Our atom-swapping efforts were mentioned in Nature!
• Mar 2023 - Our work on atom-swapping reactions as part of recent developments in skeletal editing is highlighted in Chemistry World.
• Nov 2022 - We say goodbye to Quang and wish him all the best for the future.
• Sep 2022 - Tian's paper on Ni(cod)(DQ)-catalyzed C-N coupling is online! A few good control experiments led to a convenient synthetic method.
• Aug 2022 - We say goodbye to Ne and wish him all the best at MIT.
• Jul 2022 - Our group's projects on atom swapping have received NIH funding under the MIRA ESI program!
• Feb 2022 - Our C-to-O atom swapping reaction sequence is highlighted in Chemistry World.
• Jan 2022 - Our first paper on atom swapping is published!