(Z)-selective Takai olefination of salicylaldehydes
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Peer-reviewed
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Abstract
The Takai olefination (or Takai reaction) is a method for the conversion of aldehydes to vinyl iodides, and has seen widespread implementation in organic synthesis. The reaction is usually noted for its high (E)-selectivity; however, herein we report the highly (Z)-selective Takai olefination of salicylaldehyde derivatives. Systematic screening of related substrates led to the identification of key factors responsible for this surprising inversion of selectivity, and enabled the development of a modified mechanistic model to rationalise these observations.
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Keywords
Takai olefination, alkenyl iodides, salicylaldehydes, stereoselectivity, transition state
Journal Title
Beilstein Journal of Organic Chemistry
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1860-5397
1860-5397
1860-5397
Volume Title
13
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Beilstein-Institut
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Sponsorship
Royal Society (WM150022)
Engineering and Physical Sciences Research Council (EP/J016012/1)
Engineering and Physical Sciences Research Council (EP/P020291/1)
European Research Council (279337)
Engineering and Physical Sciences Research Council (EP/J016012/1)
Engineering and Physical Sciences Research Council (EP/P020291/1)
European Research Council (279337)
The research leading to these results has received funding from the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013)/ERC grant agreement no [279337/DOS]. In addition, the group research was supported by grants from the Engineering and Physical Sciences Research Council, Biotechnology and Biological Sciences Research Council, Medical Research Council and Wellcome Trust.