Ruthenium-catalysed Z-selective cross metathesis of allylic-substituted olefins† †Electronic supplementary information (ESI) available: Experimental procedures and spectroscopic data for all new compounds. See DOI: 10.1039/c3sc52806e Click here for additional data file.

نویسندگان

  • Brendan L. Quigley
  • Robert H. Grubbs
چکیده

The Z-selective cross metathesis of allylic-substituted olefins is explored with recently developed ruthenium-based metathesis catalysts. The reaction proceeds with excellent stereoselectivity for the Z-isomer (typically >95%) and yields of up to 88% for a variety of allylic substituents. This includes the first synthesis of Z-α,β-unsaturated acetals by cross metathesis and their elaboration to Z-α,β-unsaturated aldehydes. In addition, the reaction is tolerant of a variety of cross partners, varying in functionality and steric profile.

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منابع مشابه

Introducing unactivated acyclic internal aliphatic olefins into a cobalt catalyzed allylic selective dehydrogenative Heck reaction† †Electronic supplementary information (ESI) available. CCDC 1507233. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc01204g Click here for additional data file. Click here for additional data file.

Unactivated acyclic internal aliphatic olefins are often found to be unreactive in conventional alkenylation reactions. To address this problem, a cobalt catalyzed allylic selective dehydrogenative Heck reaction with internal aliphatic olefins has been developed. The method is highly regioand stereoselective, the conditions are mild and a wide variety of functional groups can be tolerated. Rema...

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عنوان ژورنال:

دوره 5  شماره 

صفحات  -

تاریخ انتشار 2014