Journal of the American Chemical Society p. 3979 - 3982 (1988)
Update date:2022-09-26
Topics:
Roush, William R.
Banfi, Luca
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.
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