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      Stereodivergent Dual Catalytic α-Allylation of Protected α-Amino- and α-Hydroxyacetaldehydes

      , , ,
      Angewandte Chemie
      Wiley

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          Synergistic Catalysis: A Powerful Synthetic Strategy for New Reaction Development.

          Synergistic catalysis is a synthetic strategy wherein both the nucleophile and the electrophile are simultaneously activated by two separate and distinct catalysts to afford a single chemical transformation. This powerful catalysis strategy leads to several benefits, specifically synergistic catalysis can (i) introduce new, previously unattainable chemical transformations, (ii) improve the efficiency of existing transformations, and (iii) create or improve catalytic enantioselectivity where stereocontrol was previously absent or challenging. This perspective aims to highlight these benefits using many of the successful examples of synergistic catalysis found in the literature.
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            Enantio- and diastereodivergent dual catalysis: α-allylation of branched aldehydes.

            An important challenge in asymmetric synthesis is the development of fully stereodivergent strategies to access the full complement of stereoisomers of products bearing multiple stereocenters. In the ideal case, where four products are possible, applying distinct catalysts to the same set of starting materials under identical conditions would in a single step afford any given stereoisomer. Herein, we describe the realization of this concept in a fully stereodivergent dual-catalytic synthesis of γ,δ-unsaturated aldehydes bearing vicinal quaternary/tertiary stereogenic centers. The reaction is enabled by chiral iridium and amine catalysts, which activate the allylic alcohol and aldehyde substrates, respectively. Each catalyst exerts high local stereocontrol irrespective of the other's inherent preference.
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              Chiral counteranions in asymmetric transition-metal catalysis: highly enantioselective Pd/Brønsted acid-catalyzed direct alpha-allylation of aldehydes.

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                Author and article information

                Journal
                Angewandte Chemie
                Angew. Chem.
                Wiley
                00448249
                November 23 2015
                November 23 2015
                October 02 2015
                : 127
                : 48
                : 14571-14575
                Article
                10.1002/ange.201506933
                6060ffd5-d925-4e9d-b989-f6fcf6f2e501
                © 2015

                http://doi.wiley.com/10.1002/tdm_license_1.1

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