Communication
Pd-Catalyzed Cleavage of Benzylic Nitro Bonds: New Opportunities for Asymmetric Synthesis†
Thomas C. Fessard Dr.,
Hajime Motoyoshi Dr.,
Erick M. Carreira Prof. Dr.,
Thomas C. Fessard Dr.
Laboratorium für Organische Chemie, ETH Hönggerberg, 8093 Zürich, Switzerland, Fax: (+41) 1-632-1328
Search for more papers by this authorHajime Motoyoshi Dr.
Laboratorium für Organische Chemie, ETH Hönggerberg, 8093 Zürich, Switzerland, Fax: (+41) 1-632-1328
Search for more papers by this authorErick M. Carreira Prof. Dr.
Laboratorium für Organische Chemie, ETH Hönggerberg, 8093 Zürich, Switzerland, Fax: (+41) 1-632-1328
Search for more papers by this authorThomas C. Fessard Dr.,
Hajime Motoyoshi Dr.,
Erick M. Carreira Prof. Dr.,
Thomas C. Fessard Dr.
Laboratorium für Organische Chemie, ETH Hönggerberg, 8093 Zürich, Switzerland, Fax: (+41) 1-632-1328
Search for more papers by this authorHajime Motoyoshi Dr.
Laboratorium für Organische Chemie, ETH Hönggerberg, 8093 Zürich, Switzerland, Fax: (+41) 1-632-1328
Search for more papers by this authorErick M. Carreira Prof. Dr.
Laboratorium für Organische Chemie, ETH Hönggerberg, 8093 Zürich, Switzerland, Fax: (+41) 1-632-1328
Search for more papers by this author†
This work was supported by the ETH Zürich (INIT) and the Uehara Memorial Foundation (financial support to H.M.).
Graphical Abstract
Without a trace: Benzylic nitroalkanes are reduced to the corresponding parent alkanes in good yields by using a simple procedure involving heterolytic CN bond cleavage (see scheme). Traceless removal of the nitro group leaves behind a stereogenic center that may otherwise be difficult to install. This reaction significantly expands the scope of building blocks that can be accessed.
Supporting Information
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