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Synfacts 2016; 12(06): 0603
DOI: 10.1055/s-0035-1562173
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Molybdenum Complex Catalyzed Z-Selective Cross-Metathesis

Contributor(s):
Hisashi Yamamoto
,
Yasushi Shimoda
Koh MJ, Nguyen TT, Zhang H, Schrock RR, Hoveyda AH * Boston College, Chestnut Hill and Massachusetts Institute of Technology, Cambridge, USA
Direct Synthesis of Z-Alkenyl Halides through Catalytic Cross-Metathesis.

Nature 2016;
531: 459-465
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Further Information

Publication History

Publication Date:
17 May 2016 (online)

 
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Key words

molybdenum catalysis - cross-metathesis - stereoselectivity - haloalkenes

Significance

Cross-metathesis with alkenyl halides is a highly challenging problem. The authors have developed a molybdenum alkylidene species that reacts with alkenyl halides to afford various bromo-, chloro-, or fluoroalkenes with high Z-selectivities. The synthesis of biologically active compounds is also demonstrated.


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Comment

Commercially available (Z)-1-bromo-2-fluoroethene can be used as a fluoride source, instead of vinyl fluoride or (Z)-1,2-difluoroethene, which are difficult to handle. The authors suggest that, for steric and electronic reasons, the reaction with (Z)-1-bromo-2-fluoroethene proceeds through intermediate I.


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