HFIP in organic synthesis

HF Motiwala, AM Armaly, JG Cacioppo… - Chemical …, 2022 - ACS Publications
1, 1, 1, 3, 3, 3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating
solvent that has found numerous uses in organic synthesis due to its ability to stabilize ionic …

New twists in Nazarov cyclization chemistry

AJ Frontier, JJ Hernandez - Accounts of Chemical Research, 2020 - ACS Publications
Conspectus The defining feature of the Nazarov cyclization is a 4π-conrotatory
electrocyclization, resulting in the stereospecific formation of functionalized …

Total syntheses of calyciphylline A-type alkaloids (−)-10-deoxydaphnipaxianine A,(+)-daphlongamine E and (+)-calyciphylline R via late-stage divinyl carbinol …

Y Zhang, Y Chen, M Song, B Tan, Y Jiang… - Journal of the …, 2022 - ACS Publications
Among the famous Daphniphyllum alkaloids family, the calyciphylline A-type subfamily has
triggered particular interest from the organic synthesis community in recent years. Here, we …

Computational Design, Synthesis, and Photochemistry of Cy7‐PPG, an Efficient NIR‐Activated Photolabile Protecting Group for Therapeutic Applications

G Alachouzos, AM Schulte, A Mondal… - Angewandte …, 2022 - Wiley Online Library
Abstract Photolabile Protecting Groups (PPGs) are molecular tools used, for example, in
photopharmacology for the activation of drugs with light, enabling spatiotemporal control …

Brønsted Acid-Catalyzed Dehydrative Nazarov-Type Cyclization/C2–N1 Cleavage Cascade of Perfluoroalkylated 3-Indolyl (2-benzothienyl) methanols

L Feng, Y Teng, X Yu, Z Wang, W Rao - Organic Letters, 2023 - ACS Publications
A novel and unprecedented p-toluenesulfonic acid-catalyzed dehydrative Nazarov-type
cyclization/C2–N1 bond cleavage cascade reaction of perfluoroalkylated 3-indolyl (2 …

Recent advances in the interrupted Nazarov reaction

AV Yadykov, VZ Shirinian - Advanced Synthesis & Catalysis, 2020 - Wiley Online Library
In recent decades there have been significant improvements in the efficiency of synthesis as
a result of considerable progress in tandem reactions, cascade transformations and related …

Metal-free alkene carbooxygenation following tandem intramolecular alkoxylation/Claisen rearrangement: stereocontrolled access to bridged [4.2. 1] lactones

L Li, XQ Zhu, YQ Zhang, HZ Bu, P Yuan, J Chen… - Chemical …, 2019 - pubs.rsc.org
Alkene carbooxygenation has attracted considerable attention over the past few decades as
this approach provides an efficient access to various oxygen-containing molecules …

Nitrogen-interrupted halo-Prins/halo-Nazarov fragment coupling cascade for the synthesis of indolines

A Milosavljevic, C Holt, AJ Frontier - Chemical Science, 2023 - pubs.rsc.org
The nitrogen-interrupted Nazarov cyclization can be a powerful method for the
stereocontrolled synthesis of sp3-rich N-heterocycles. However, due to the incompatibility …

Alkynyl Prins carbocyclization cascades for the synthesis of linear-fused heterocyclic ring systems

JJ Hernandez, AJ Frontier - Chemical Science, 2022 - pubs.rsc.org
We report a Brønsted acid-catalyzed carbocyclization cascade, featuring condensation of an
alcohol/sulfonamide with an aldehyde followed by an intramolecular three-component …

Leveraging the Halo-Nazarov Cyclization for the Chemodivergent Assembly of Functionalized Haloindenes and Indanones

C Holt, G Alachouzos, AJ Frontier - Journal of the American …, 2019 - ACS Publications
In this report, we describe a halo-Prins/aryl halo-Nazarov cyclization strategy that employs
readily available starting materials, inexpensive reagents, and convenient reaction …