Horner-Wads worth-Emmons reaction

The preparation of 3-vinylpyrroles was investigated utilizing the Horner-Wads worth-Emmons reaction with 3-formyl-lV-tosylpyrrole <06S1494>. The intramolecular acylation of pyrrole-2-Weinreb amides provided access to novel indolizinone derivatives <06T6182>. The amidation of pyrrole-2-carbonyl chloride was utilized as a key step in the preparation of pyrrole-oxazole analogue 90 of the insecticide Pirate <06S1975>. 

In conclusion, a catalytic asymmetric Horner-Wads worth-Emmons reaction using chinchona derivatives as organocatalysts has recently been realized. Because enantioselectivity is currently low to modest, improvement of the reaction to make this route attractive for asymmetric preparation of enantiomerically pure enones of type 77 is certainly a major issue. 

Desymmetriza-tion of prochiral ketone via Horner-Wads-worth-Emmons reaction... 

C Johnson, B Zhang. Solid phase synthesis of alkenes using the Horner-Wads-worth-Emmons reaction and monitoring by gel phase P NMR. Tetrahedron Lett 36 9253-9256, 1995. 

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