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Practical Synthetic Procedures for the Iron-Catalyzed Intermolecular Olefin Aminohydroxylation Using Functionalized
Cheng-Liang Zhu1, Deng-Fu Lu1, Jeffrey D Sears1
1Department of Chemistry, Georgia State University, 100 Piedmont Avenue SE, Atlanta, GA 30303, USA.
Synthesis
|January 17, 2017
Summary
This study presents practical, gram-scale iron-catalyzed olefin aminohydroxylation methods using a stable hydroxylamine reagent. The new approach expands substrate scope and yields complementary amino alcohol products.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Olefin aminohydroxylation is a key transformation for synthesizing amino alcohols.
- Existing methods often have limitations in substrate scope and reagent stability.
Purpose of the Study:
- To develop practical, gram-scale synthetic procedures for iron-catalyzed intermolecular olefin aminohydroxylation.
- To introduce a bench-stable functionalized hydroxylamine as an effective amination reagent.
Main Methods:
- Iron-catalyzed reaction of olefins with a functionalized hydroxylamine.
- Optimization of reaction conditions for gram-scale synthesis.
Main Results:
- Successful implementation of intermolecular olefin aminohydroxylation in gram scale.
- Demonstrated compatibility with a broad range of olefins, including challenging substrates.
- Generation of amino alcohol building blocks with diverse regio- and stereo-chemical arrangements.
Conclusions:
- The developed method offers a practical and versatile approach to olefin aminohydroxylation.
- The use of a stable hydroxylamine reagent enhances the utility of this transformation.
- This method provides access to valuable amino alcohols complementary to existing synthetic strategies.
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