179112-57-3Relevant academic research and scientific papers
High stereoselectivity in the Wittig reaction induced by the interaction of charges
Klar, Ulrich,Deicke, Peter
, p. 4141 - 4144 (1996)
The synthesis of carbacyclin analogues I based on the introduction of an α-chain to a suitable substituted bicyclo[3.3.0]octan-3-one derivative like 5 by a Wittig reaction leads generally to nearly 1:1-mixtures of E/Z-isomers. This lack of selectivity will change dramatically, if an acidic sulfonamide in the bicyclic framework is present. The observed Z-selectivity can be explained by an interaction of charges of the deprotonated sulfonamide and the electrophilic phosphorous atom in the Wittig reagent.
