Switching regioselectivity in the allylation of imines by N-side chain tuning.
A spectacular inversion of α- to γ-regioselectivity in the allylzincation of imines can be achieved by fine-tuning of the N-side chain. This approach allows easy preparation of regioisomeric amines, in racemic as well as enantiopure forms. The usefulness of the method is illustrated by the parallel asymmetric syntheses of 2,3- and 2,5-diphenylpyrrolidines.
Institut de Chimie Moléculaire de Reims, CNRS (UMR 7312) and Université de Reims, 51687 Reims Cedex 2, France.
Pierre-Olivier
PO
Delaye
Jean-Luc
JL
Vasse
Jan
J
Szymoniak
D000588:Amines / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis; D013237:Stereoisomerism
D000588:Amines; D007097:Imines; D011759:Pyrrolidines; C032519:pyrrolidine