Synthesis of E- and Z-trisubstituted alkenes by catalytic cross-metathesis

Thach T. Nguyen, Ming Joo Koh, Tyler J. Mann, Richard R. Schrock and Amir H. Hoveyda ()
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Thach T. Nguyen: Merkert Chemistry Center, Boston College, Chestnut Hill
Ming Joo Koh: Merkert Chemistry Center, Boston College, Chestnut Hill
Tyler J. Mann: Merkert Chemistry Center, Boston College, Chestnut Hill
Richard R. Schrock: Massachusetts Institute of Technology, Cambridge
Amir H. Hoveyda: Merkert Chemistry Center, Boston College, Chestnut Hill

Nature, 2017, vol. 552, issue 7685, 347-354

Abstract: Abstract Catalytic cross-metathesis is a central transformation in chemistry, yet corresponding methods for the stereoselective generation of acyclic trisubstituted alkenes in either the E or the Z isomeric forms are not known. The key problems are a lack of chemoselectivity—namely, the preponderance of side reactions involving only the less hindered starting alkene, resulting in homo-metathesis by-products—and the formation of short-lived methylidene complexes. By contrast, in catalytic cross-coupling, substrates are more distinct and homocoupling is less of a problem. Here we show that through cross-metathesis reactions involving E- or Z-trisubstituted alkenes, which are easily prepared from commercially available starting materials by cross-coupling reactions, many desirable and otherwise difficult-to-access linear E- or Z-trisubstituted alkenes can be synthesized efficiently and in exceptional stereoisomeric purity (up to 98 per cent E or 95 per cent Z). The utility of the strategy is demonstrated by the concise stereoselective syntheses of biologically active compounds, such as the antifungal indiacen B and the anti-inflammatory coibacin D.

Date: 2017
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DOI: 10.1038/nature25002

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