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Synfacts 2019; 15(05): 0517
DOI: 10.1055/s-0037-1611489
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

The Jacobsen Epoxidation

Contributor(s):
Mark Lautens
,
Egor M. Larin
Jacobsen EN. * Zhang W, Muci AR, Ecker JR, Deng L. Harvard University, Cambridge, USA
Highly Enantioselective Epoxidation Catalysts Derived from 1,2-Diaminocyclohexane.

J. Am. Chem. Soc. 1991;
113: 7063-7064
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Publication History

Publication Date:
15 April 2019 (online)

 
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Key words

alkenes - manganese catalysis - enantioselective epoxidation

Significance

Although manganese-catalyzed enantioselective epoxidation of nonactivated alkenes had been previously described by Jacobsen (J. Am. Chem. Soc. 1990, 112, 2801) and Katsuki (Tetrahedron: Asymmetry 1991, 2, 481), this report was the first general and highly enantioselective method to achieve this transformation. When compared to the Sharpless epoxidation, this method does not require allylic alcohols and works best with cis-alkenes.


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Comment

Jacobsen found that by optimizing the size of the salen ligand, the approach of the olefin towards the metal center could be controlled. Thus, the bulky tert-butyl groups on the aromatic rings of the salen ligand limit the chance of competing approaches to the substrate.


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