112897-00-4Relevant academic research and scientific papers
N,N'-Dibenzyl-N,N'-ethylenetartramide: A Rationally Designed Chiral Auxiliary for the Allylboration Reaction
Roush, William R.,Banfi, Luca
, p. 3979 - 3982 (2007/10/02)
The chiral auxiliary designated in the title was designed as a probe of our previously suggested mechnism of asymmetric induction with tartrate allylboronates 1-3, namely that n/n electronic repulsive interactions between electron pairs on the aldehydic oxygen atom and an ester carbonyl disfavor transition-state C relative to A.The results reported for the new reagent 5 strongly support this thesis and suggest that the convergence of functional groups toward a metal center can be an exceedingly useful strategy for achieving a topological bias in the enantioselective functionalization of a carbonyl group.
