Stereoselective allylation of ketones: explanation for the unusual inversion of the induced stereochemistry in the auxiliary-mediated crotylation and pentenylation of butanone by DFT calculations.

Auxiliary-mediated domino crotylations and pentenylations of butanone yield homoallylic ethers with two newly formed stereogenic centers. With our norpseudoephedrine-derived auxiliary, we observed the formation of anti isomers exclusively, and the nature of the major isomer was independent of the substrate double bond geometry. Interestingly, there is a… CONTINUE READING