The Horner-Wadsworth-Emmons Reaction and Related Olefinations

The Horner-Wadsworth-Emmons Reaction and Related Olefinations 

The use of the Horner-Wadsworth-Emmons reaction for stereocontrolled olefin syn- thesis in the field of natural products has been reviewed in 2000-2013. ( ) 

The modified Julia olefination of aromatic aldehydes with alkyl benzothiazol-2-yl sul-fones has been investigated experimentally, and by DFT, with a view to identifying the origin of the high F-selectivity. The reversibility of the addition is very variable, so the selectivity of the formation of the sulfinate intermediate also varies. However, the syn- and anri-sulfinates both eliminate in concerted processes syn- and anri-periplanar, respectively), thus leading preferentially to ( )-alkene. 

The mechanism of reaction of the silylated phosphorane, Bu3P=CH-TMS, with para-substimted benzaldehydes, yielding cinnamylphosphonium salts, has been studied to 

For another route to HWE products, see under the section titled Oximes . 

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