An Efficient Protocol for the Cross-Metathesis of Sterically Demanding Olefins

Authors Zhen J. Wang, W. Roy Jackson and Andrea J. Robinson
Published Organic Letters
Graphical abstract  

OL abstract

Abstract

We have recently described synthetic routes to the azaspirocyclic ring systems found in marine tricyclic alkaloids such as Cylindricine A utilising a Ru-alkylidene cross-metathesis reaction and acid-catalysed cyclisation. Construction of the third ring, however, requires cross coupling of a highly hindered, α-substituted methylenecycloalkane. CM of such olefins is highly challenging. This paper describes a generic steric-reversal strategy that can be used to react previously unreactive, sterically demanding alkenes using commercially available catalyst.

Citation J. Wang, W. R. Jackson, A. J. Robinson, Organic Letters, 2013, 15(12), 3006-3009.
Pdf Article
Doi DOI: 10.1021/ol401194h
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