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 …

Organocatalytic Enantioselective Conia‐Ene‐Type Carbocyclization of Ynamide Cyclohexanones: Regiodivergent Synthesis of Morphans and Normorphans

Y Xu, Q Sun, TD Tan, MY Yang, P Yuan… - Angewandte Chemie …, 2019 - Wiley Online Library
Described herein is an organocatalytic enantioselective desymmetrizing cycloisomerization
of arylsulfonyl‐protected ynamide cyclohexanones, representing the first metal‐free …

Stereodivergent coupling of 1, 3-dienes with aldimine esters enabled by synergistic Pd and Cu catalysis

Q Zhang, H Yu, L Shen, T Tang, D Dong… - Journal of the …, 2019 - ACS Publications
Herein we describe the use of synergistic Pd and Cu catalysis for stereodivergent coupling
reactions between 1, 3-dienes and aldimine esters. By using different enantiomers of the two …

Asymmetric anti-Selective Borylalkylation of Terminal Alkynes by Nickel Catalysis

C Huang, D Wu, Y Li, G Yin - Journal of the American Chemical …, 2023 - ACS Publications
Selective transformation of alkyne triple bonds to double bonds serves as an efficient
platform to construct substituted alkenes. While significant advances have been made in its …

Enantioselective total synthesis of (−)-himalensine a via a palladium and 4-hydroxyproline co-catalyzed desymmetrization of vinyl-bromide-tethered cyclohexanones

R Kučera, SR Ellis, K Yamazaki… - Journal of the …, 2023 - ACS Publications
Herein, we describe the convergent enantioselective total synthesis of himalensine A in 18
steps, enabled by a highly enantio-and diastereoselective construction of the morphan core …

Switchable, Reagent‐Controlled Diastereodivergent Photocatalytic Carbocyclisation of Imine‐Derived α‐Amino Radicals

JAP Maitland, JA Leitch, K Yamazaki… - Angewandte Chemie …, 2021 - Wiley Online Library
A reagent‐controlled stereodivergent carbocyclisation of aryl aldimine‐derived,
photocatalytically generated, α‐amino radicals possessing adjacent conjugated alkenes …

Iridium-Catalyzed Intramolecular β-C–H Alkenylation of Ketones with Alkynes via a Hydride-Transfer Approach

B Zhou, S Deng, Y Xu, X Qi, G Dong - Journal of the American …, 2022 - ACS Publications
Direct functionalization of carbonyl β C–H bonds without using directing groups has not
been a trivial task, and it is even more challenging to realize the corresponding atom …

Enantioselective access to γ-all-carbon quaternary center-containing cyclohexanones by palladium-catalyzed desymmetrization

Q Wei, J Cai, XD Hu, J Zhao, H Cong, C Zheng… - ACS …, 2019 - ACS Publications
An efficient desymmetrization of γ-quaternary carbon-containing cyclohexanones using
readily available Pd/(S)-t BuPhox and benzylamine as dual catalysts is reported. We …

Palladium (0)/benzoic acid catalysis merges sequences with D 2 O-promoted labelling of C–H bonds

G Cera, N Della Ca, G Maestri - Chemical Science, 2019 - pubs.rsc.org
The combination of a Pd (0) complex with benzoic acid in the presence of D2O enables the
synthesis of valuable families of highly deuterated organics through elaborate sequential …

Synergistic Homogeneous Asymmetric Cu Catalysis with Pd Nanoparticle Catalysis in Stereoselective Coupling of Alkynes with Aldimine Esters

Y Liu, H Chen, X Wang - Journal of the American Chemical …, 2024 - ACS Publications
Understanding the nature of a transition-metal-catalyzed process, including catalyst
evolution and the real active species, is rather challenging yet of great importance for the …