1. Recent Advances in Stereoselective [2+2+2] Cycloadditions
- Author
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Amatore, Muriel, Aubert, Corinne, Méthodes et Application en Chimie Organique (MACO), Institut Parisien de Chimie Moléculaire (IPCM), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Universite Pierre et Marie Curie-Paris 6, Centre National de la Recherche Scientifique (CNRS), and Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
- Subjects
Polycycles ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,Asymmetric synthesis ,Cyclotrimerization ,Transition metals ,Chirality - Abstract
International audience; The [2+2+2] cycloaddition reaction is considered one of the most efficient methods for the rapid and straightforward preparation of complex polycyclic (and heterocyclic) compounds in a highly selective and atom-economical fashion. Over the last half-century, remarkable advances in terms of chemo-and regioselectivities have been realized, endowing this reaction with attractive features as a key step in the synthesis of various biologically active molecules and materials. The development of stereoselective methodologies is more recent. In this field, asymmetric transition-metal catalysis has emerged as the most convenient tool with which to perform these [2+2+2] cycloadditions in their enantio-and diastereo-selective variants. All the catalytic systems that have been developed so far are based on very close association of a transition metal (Co, Ni, Ir, Rh,...) with a chiral ligand. The success of these reactions is then related to the reaction pattern involved (inter-and intramolecular), implying an efficient substrate/active species interaction. Thus, judicious design both of chiral ligands and of unsaturated substrates is necessary. In light of these aspects, numerous stereoselective cycloadditions have been reported; these allow the construction in one-step fashion of central, axial, planar, and helical chiralities. This review details the recent advances in this area, with specific attention to catalysts and reaction scope.
- Published
- 2015
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