Chemo- and Regioselective Functionalization of Polyols through Catalytic C(sp3
)–C(sp3) Kumada-Type Coupling of Cyclic Sulfate Esters

Ramírez-Contreras, Rodrigo; Morandi, Bill

doi:10.1021/acs.orglett.6b01745

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Chemo- and Regioselective Functionalization of Polyols through Catalytic C(sp³)–C(sp³) Kumada-Type Coupling of Cyclic Sulfate Esters

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Ramírez-Contreras, Rodrigo
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Morandi, Bill
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Ramírez-Contreras, R., & Morandi, B. (2016). Chemo- and Regioselective Functionalization of Polyols through Catalytic C(sp³)–C(sp³) Kumada-Type Coupling of Cyclic Sulfate Esters. Organic Letters, 18(15), 3718-3721. doi:10.1021/acs.orglett.6b01745.

Cite as: https://hdl.handle.net/11858/00-001M-0000-002B-A61A-B

Abstract

This contribution describes a copper-catalyzed, C(sp³)–C(sp³) cross-coupling reaction of cyclic sulfate esters, a distinct class of electrophilic derivatives of polyols, with alkyl Grignard reagents to afford functionalized alcohol products in good yields. The method is operationally simple and highlights the potential of cyclic sulfate esters as highly reactive substrates in catalytic, chemoselective polyol transformations.