( Z )-Selective Takai olefination of salicylaldehydes

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 ( )-selectivity; however, herein we report the highly ( )-selective Takai olefination of sal...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2017-02, Vol.13 (1), p.323-328
Main Authors: Geddis, Stephen M, Hagerman, Caroline E, Galloway, Warren R J D, Sore, Hannah F, Goodman, Jonathan M, Spring, David R
Format: Article
Language:English
Subjects:
Aldehydes
alkenyl iodides
Chemistry
Letter
Ligands
Ratios
salicylaldehydes
stereoselectivity
Takai olefination
transition state
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Summary: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 ( )-selectivity; however, herein we report the highly ( )-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.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.13.35