The Dong Group develops new synthetic reactions through mechanistic understanding and molecular design. Our research centers on two complementary themes: stereospecific transformations that translate existing chirality into molecular complexity, and main-group catalysis that enables new pathways for selective bond formation and cleavage.

 

 

  1. Stereospecific Reactions: Stereochemical Inheritance through New Reactivity

 

Chirality as a synthetic resource

 

We develop reactions in which the stereochemistry of a starting material determines that of the product. This strategy treats chirality as information to be transferred through a chemical transformation, rather than recreated at each stage of synthesis. Stereochemical inheritance can involve either retention or predictable inversion of configuration; the essential requirement is a well-defined relationship between substrate and product stereochemistry.

 

Stereospecific synthesis complements asymmetric catalysis. Advances in asymmetric synthesis, together with naturally occurring chiral compounds, provide access to diverse enantioenriched starting materials. Yet many transformations activate these molecules through intermediates that lose their stereochemical information. Our goal is to preserve and repurpose this embedded chirality while expanding the reactions available for molecular construction.

 

This approach is particularly appealing when asymmetric recognition must distinguish closely similar substituents. Instead of asking a chiral catalyst to discriminate between methyl, ethyl, and propyl groups during bond formation, we seek to inherit the required configuration from an appropriate starting material. This allows reaction development to focus on new modes of activation and chemoselectivity while maintaining stereochemical fidelity.

 

 

Proximity and mutual activation

 

A central question guides our reaction design: can productive bond formation outpace stereochemical scrambling? Reactive intermediates need not be indefinitely configurationally stable to transmit stereochemical information. They must instead undergo the desired transformation before competing processes erase that information.

 

We explore proximity-induced kinetic preference as a means of controlling this competition. By organizing reactive partners before or during activation, we aim to favor rapid bond formation over racemization. Lewis acid–base interactions provide a framework for mutual activation, bringing electrophilic and nucleophilic partners together within a reactive assembly. This strategy connects substrate activation with spatial organization and offers a way to extend proximity-controlled chemistry beyond substrates with pre-existing intramolecular connections.

 

Our interest is not limited to preserving chirality in familiar reactions. Bringing reactive intermediates into close proximity may also enable transformations that are difficult to achieve through conventional intermolecular encounters. We therefore view stereochemical control and reaction discovery as interconnected objectives.

 

Bond construction and skeletal reorganization

 

Our work on chiral epoxides illustrates how stereospecific reactivity connects functional-group activation with molecular construction. The enantiospecific homo-boron–Wittig reaction converts chiral epoxides into cyclopropanes through stereoinvertive intramolecular substitution. Related organozinc chemistry enables triatropic rearrangements and ring contraction; its combination with Diels–Alder cycloaddition provides a formal [4+2–1] strategy for constructing chiral cyclopentanes. These transformations demonstrate how controlled stereochemical transfer can accompany substantial changes in molecular architecture.

 

We seek to broaden this principle across carbon–carbon bond formation and skeletal reorganization, with particular interest in readily accessible chiral alcohols and their derivatives. Our long-term objective is to make stereochemical inheritance a general tool for synthesis: establish chirality through an effective available method, then carry that information into structurally distinct products. By connecting accessible chiral feedstocks with new reactivity, we aim to expand the range of molecules that can be prepared with predictable stereochemical outcomes.

 

 

  1. Main-Group Catalysis: Discovering New Reactivity

 

New activation modes

 

We explore main-group elements as catalytic centers for selective chemical transformations, with particular interest in germanium and antimony. Our goal is not simply to replace a familiar catalyst with a different element, but to identify reaction pathways enabled by the electronic structure and coordination chemistry of the main-group center.

 

Molecular design is central to this effort. We investigate how organic frameworks, substituents, and coordination environments influence substrate activation, intermediate reactivity, and catalyst regeneration. These relationships guide the search for new catalytic bond-cleavage and bond-forming processes. An important question is how coordination can redirect reactive intermediates toward productive transformations rather than unproductive binding or catalyst deactivation. This perspective connects Lewis acid activation with radical chemistry and motivates our exploration of cooperative catalysis.

 

RESEARCH

The Dong Group develops new synthetic reactions through mechanistic understanding and molecular design. Our research centers on two complementary themes: stereospecific transformations that translate existing chirality into molecular complexity, and main-group catalysis that enables new pathways for selective bond formation and cleavage.

 

 

  1. Stereospecific Reactions: Stereochemical Inheritance through New Reactivity

 

Chirality as a synthetic resource

 

We develop reactions in which the stereochemistry of a starting material determines that of the product. This strategy treats chirality as information to be transferred through a chemical transformation, rather than recreated at each stage of synthesis. Stereochemical inheritance can involve either retention or predictable inversion of configuration; the essential requirement is a well-defined relationship between substrate and product stereochemistry.

 

Stereospecific synthesis complements asymmetric catalysis. Advances in asymmetric synthesis, together with naturally occurring chiral compounds, provide access to diverse enantioenriched starting materials. Yet many transformations activate these molecules through intermediates that lose their stereochemical information. Our goal is to preserve and repurpose this embedded chirality while expanding the reactions available for molecular construction.

 

This approach is particularly appealing when asymmetric recognition must distinguish closely similar substituents. Instead of asking a chiral catalyst to discriminate between methyl, ethyl, and propyl groups during bond formation, we seek to inherit the required configuration from an appropriate starting material. This allows reaction development to focus on new modes of activation and chemoselectivity while maintaining stereochemical fidelity.

 

 

Proximity and mutual activation

 

A central question guides our reaction design: can productive bond formation outpace stereochemical scrambling? Reactive intermediates need not be indefinitely configurationally stable to transmit stereochemical information. They must instead undergo the desired transformation before competing processes erase that information.

 

We explore proximity-induced kinetic preference as a means of controlling this competition. By organizing reactive partners before or during activation, we aim to favor rapid bond formation over racemization. Lewis acid–base interactions provide a framework for mutual activation, bringing electrophilic and nucleophilic partners together within a reactive assembly. This strategy connects substrate activation with spatial organization and offers a way to extend proximity-controlled chemistry beyond substrates with pre-existing intramolecular connections.

 

Our interest is not limited to preserving chirality in familiar reactions. Bringing reactive intermediates into close proximity may also enable transformations that are difficult to achieve through conventional intermolecular encounters. We therefore view stereochemical control and reaction discovery as interconnected objectives.

 

Bond construction and skeletal reorganization

 

Our work on chiral epoxides illustrates how stereospecific reactivity connects functional-group activation with molecular construction. The enantiospecific homo-boron–Wittig reaction converts chiral epoxides into cyclopropanes through stereoinvertive intramolecular substitution. Related organozinc chemistry enables triatropic rearrangements and ring contraction; its combination with Diels–Alder cycloaddition provides a formal [4+2–1] strategy for constructing chiral cyclopentanes. These transformations demonstrate how controlled stereochemical transfer can accompany substantial changes in molecular architecture.

 

We seek to broaden this principle across carbon–carbon bond formation and skeletal reorganization, with particular interest in readily accessible chiral alcohols and their derivatives. Our long-term objective is to make stereochemical inheritance a general tool for synthesis: establish chirality through an effective available method, then carry that information into structurally distinct products. By connecting accessible chiral feedstocks with new reactivity, we aim to expand the range of molecules that can be prepared with predictable stereochemical outcomes.

 

 

  1. Main-Group Catalysis: Discovering New Reactivity

 

New activation modes

 

We explore main-group elements as catalytic centers for selective chemical transformations, with particular interest in germanium and antimony. Our goal is not simply to replace a familiar catalyst with a different element, but to identify reaction pathways enabled by the electronic structure and coordination chemistry of the main-group center.

 

Molecular design is central to this effort. We investigate how organic frameworks, substituents, and coordination environments influence substrate activation, intermediate reactivity, and catalyst regeneration. These relationships guide the search for new catalytic bond-cleavage and bond-forming processes. An important question is how coordination can redirect reactive intermediates toward productive transformations rather than unproductive binding or catalyst deactivation. This perspective connects Lewis acid activation with radical chemistry and motivates our exploration of cooperative catalysis.