Asymmetric synthesis of proline-based conformationally constrained tryptophan mimetic
Pierre-Olivier Delaye1, Jean-Luc Vasse, Jan Szymoniak
1ICMR, CNRS-UMR 6229, Université de Reims Champagne-Ardenne, BP 1039, 51687, Reims Cedex 2, France.
Abstract:
The synthesis of an optically pure proline-based tryptophan mimetic is described. The strategy involves the in situ generation of an unprecedented allylmetal species containing the indole moiety, and its coupling with a chiral imine. The construction of the 3-substituted proline skeleton is then achieved through a hydrozirconation/iodination sequence applied to the resulting homoallylic amine.
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