Concepedia

Enantioselective Linchpin Catalysis by SOMO Catalysis: An Approach to the Asymmetric α‐Chlorination of Aldehydes and Terminal Epoxide Formation

Muriel Amatore, T. D. Beeson, Sean P. Brown, David W. C. MacMillan

Angewandte Chemie International Edition · 2009 · 193 citations · 24 references

DOI

Concepts

Abstract

Time for SOme MOre: For the first time SOMO (singly occupied molecular orbital) activation has been exploited to allow a new approach to the alpha-chlorination of aldehydes. This transformation can be readily implemented as part of a linchpin catalysis approach to the enantioselective production of terminal epoxides.

References

24

Merging Photoredox Catalysis with Organocatalysis: The Direct Asymmetric Alkylation of Aldehydes

David A. Nicewicz, David W. C. MacMillan · Science · 2008 · 2.4K citations · Full text

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Highly Selective Hydrolytic Kinetic Resolution of Terminal Epoxides Catalyzed by Chiral (salen)Co<sup>III</sup>Complexes. Practical Synthesis of Enantioenriched Terminal Epoxides and 1,2-Diols

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Enantioselective Organo-Cascade Catalysis

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Asymmetric Organocatalytic Epoxidation of α,β-Unsaturated Aldehydes with Hydrogen Peroxide

Mauro Marigo, Johan Franzén, Thomas B. Poulsen et al. · Journal of the American Chemical Society · 2005 · 451 citations

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Polymer-Supported Chiral Co(Salen) Complexes:  Synthetic Applications and Mechanistic Investigations in the Hydrolytic Kinetic Resolution of Terminal Epoxides

D. Allen Annis, Eric N. Jacobsen · Journal of the American Chemical Society · 1999 · 426 citations

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