Switchable supramolecular helices for asymmetric stereodivergent catalysis

Area of Science:

• Supramolecular Chemistry
• Asymmetric Catalysis
• Organic Synthesis

Background:

• Controlling multiple stereogenic centers in a single molecule remains a challenge.
• Existing dynamic catalysts lack the ability for in-situ control of multiple stereocenters.

Purpose of the Study:

• To develop a switchable asymmetric catalyst for controlling multiple stereogenic centers.
• To demonstrate the synthesis of specific stereoisomers of amino alcohols.

Main Methods:

• Utilized hydrogen-bonded assemblies of benzene-1,3,5-tricarboxamide (BTA) components.
• Employed a copper-hydride catalyzed hydrosilylation and hydroamination cascade reaction.
• Manipulated supramolecular helix handedness to direct stereoisomer formation.

Main Results:

• Achieved majority synthesis of any of the four possible stereoisomers of an amino alcohol.
• Demonstrated predictable control over product stereochemistry by altering catalyst helix handedness.
• Obtained stereoisomers in a one-pot manner or sequentially by switching helix handedness.

Conclusions:

• Supramolecular helical catalysts offer a versatile platform for controlling molecular configuration.
• This strategy enables precise control over multiple stereogenic centers in a single scaffold.
• The developed catalyst provides a novel approach to asymmetric synthesis.