Volume 57, Issue 15 pp. 3981-3984
Communication

Chemoselective Synthesis of Z-Olefins through Rh-Catalyzed Formate-Mediated 1,6-Reduction

Raphael Dada

Raphael Dada

Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 Canada

These authors contributed equally to this work.

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Zhongyu Wei

Zhongyu Wei

Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 Canada

These authors contributed equally to this work.

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Ruohua Gui

Ruohua Gui

Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 Canada

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Prof. Rylan J. Lundgren

Corresponding Author

Prof. Rylan J. Lundgren

Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 Canada

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First published: 13 February 2018
Citations: 17

Graphical Abstract

Two become one: Many prevailing methods for cis-olefination are complicated by the presence of multiple unsaturated units or electrophilic functional groups. In this study, Z-olefins are delivered through selective reduction of activated dienes using formic acid. The reaction proceeds with high regio- and stereoselectivity (typically >90:10 and >95:5, respectively) and preserves other alkenyl, alkynyl, protic, and electrophilic groups.

Abstract

Z-olefins are important functional units in synthetic chemistry; their preparation has thus received considerable attention. Many prevailing methods for cis-olefination are complicated by the presence of multiple unsaturated units or electrophilic functional groups. In this study, Z-olefins are delivered through selective reduction of activated dienes using formic acid. The reaction proceeds with high regio- and stereoselectivity (typically >90:10 and >95:5, respectively) and preserves other alkenyl, alkynyl, protic, and electrophilic groups.

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