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Synfacts 2011(6): 0623-0623  
DOI: 10.1055/s-0030-1260444
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Z-Selective Olefin Cross-Metathesis

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
S. J. Meek, R. V. O’Brien, J. Llaveria, R. R. Schrock, A. H. Hoveyda*
Boston College, Chestnut Hill and Massachusetts Institute of Technology, Cambridge, USA
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Publication History

Publication Date:
19 May 2011 (online)

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Significance

Selective formation of Z-disubstituted alkenes is an important synthetic problem, which is nonetheless poorly explored. In this ­paper, the authors developed molybdenum-­mediated scalable Z-selective cross-metathesis protocols, involving terminal enol ethers (never ­reported in cross-metathesis so far) and allylic amides (previously known to provide E-selectivity only). The synthetic utility of the developed methodologies was exemplified by implementation thereof in the total syntheses of biologically im­portant products C18 (plasm)-16:0 (PC) and KRN7000. The paper provides detailed considerations of mechanistic details and methodological challenges associated with them.