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      Diastereodivergent Synthesis of β‐Amino Alcohols by Dual‐Metal‐Catalyzed Coupling of Alkoxyallenes with Aldimine Esters

      1 , 1 , 1
      Angewandte Chemie International Edition
      Wiley

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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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            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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              Intramolecular dipolar cycloaddition reactions of azomethine ylides.

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                Author and article information

                Contributors
                Journal
                Angewandte Chemie International Edition
                Angew. Chem. Int. Ed.
                Wiley
                1433-7851
                1521-3773
                March 15 2021
                February 03 2021
                March 15 2021
                : 60
                : 12
                : 6545-6552
                Affiliations
                [1 ]State Key Laboratory and Institute of Elemento-Organic Chemistry College of Chemistry Nankai University Tianjin 300071 China
                Article
                10.1002/anie.202014510
                7ac60136-4b55-432a-bfc0-4089988c2d32
                © 2021

                http://onlinelibrary.wiley.com/termsAndConditions#vor

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

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