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A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling
Shengyang Ni1, Alberto F Garrido-Castro1, Rohan R Merchant1
1Scripps Research, North Torrey Pines Road, La Jolla, CA, 92037, USA.
Angewandte Chemie (International Ed. in English)
|September 14, 2018
Summary
This study introduces a simple radical reaction to create diverse, enantiomerically pure alpha-amino acids from carboxylic acids and chiral sulfinimines. This method efficiently produces over 85 examples, including novel structures for drug discovery.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Medicinal Chemistry
Background:
- Accessing enantiomerically pure alpha-amino acids is crucial for drug development.
- Existing synthetic methods can be complex or limited in scope.
Purpose of the Study:
- To develop a straightforward and modular method for synthesizing a wide range of enantiomerically pure alpha-amino acids.
- To enable the creation of both known and novel amino acid structures.
Main Methods:
- A radical-based direct union reaction between primary, secondary, and tertiary carboxylic acids and a chiral glyoxylate-derived sulfinimine.
- Utilized operational simplicity for efficient synthesis.
Main Results:
- Successfully synthesized over 85 examples of enantiomerically pure alpha-amino acids.
- Demonstrated modular assembly of diverse and exotic amino acid structures.
- Validated the method's utility in high-throughput library synthesis.
Conclusions:
- The developed radical reaction offers rapid access to valuable enantiomerically pure alpha-amino acids.
- The method's simplicity and modularity make it suitable for medicinal chemistry applications.
- Implementation in three medicinal chemistry campaigns highlights its practical significance.
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