SPHENOL, A New Chiral Framework for Asymmetric Synthesis
Ronghua Zhang1, Shulin Ge1, Jianwei Sun1,2
1Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China.
Journal of the American Chemical Society
|August 6, 2021
Summary
Researchers developed SPHENOL, a novel chiral framework combining BINOL and SPINOL advantages. This versatile new platform shows great potential for advancing asymmetric synthesis through various catalytic applications.
Area of Science:
- Organic Chemistry
- Catalysis
- Asymmetric Synthesis
Background:
- Privileged chiral catalysts are crucial for asymmetric synthesis, but limited frameworks exist.
- Developing new, versatile chiral scaffolds is essential but challenging.
Purpose of the Study:
- To design, synthesize, and evaluate a novel chiral framework, SPHENOL.
- To explore SPHENOL's potential as a platform for new chiral ligands and catalysts.
Main Methods:
- Design and synthesis of the SPHENOL chiral framework.
- Application of SPHENOL-derived catalysts in asymmetric hydrogenation, hydroacylation, and spirocyclization reactions.
Main Results:
- SPHENOL was successfully synthesized and demonstrated to possess combined advantages of BINOL and SPINOL.
- SPHENOL-based catalysts exhibited superior performance in mechanistically diverse asymmetric reactions.
- The practical asymmetric synthesis of SPHENOL itself was achieved.
Conclusions:
- SPHENOL represents a promising new chiral framework with broad applicability.
- Its unique structural features facilitate the development of effective chiral ligands and catalysts.
- SPHENOL has significant potential to advance the field of asymmetric synthesis.
More Related Videos
12:30Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
9.3K
10:42Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
10.0K
Related Concept Videos
02:30Chirality at Nitrogen, Phosphorus, and Sulfur
6.2K
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
6.2K
02:05Prochirality
4.2K
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
4.2K
02:26Preparation and Reactions of Sulfides
5.3K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
5.3K
02:23SN2 Reaction: Stereochemistry
10.2K
In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
10.2K
02:17Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
3.6K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.6K
02:21Naming Enantiomers
23.1K
The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system...
23.1K