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      Enantio‐ and Diastereodivergent Synthesis of Spirocycles through Dual‐Metal‐Catalyzed [3+2] Annulation of 2‐Vinyloxiranes with Nucleophilic Dipoles

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          Large-scale applications of transition metal-catalyzed couplings for the synthesis of pharmaceuticals.

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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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              Transition-metal-catalyzed C-S, C-Se, and C-Te bond formation via cross-coupling and atom-economic addition reactions.

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                Author and article information

                Contributors
                Journal
                Angewandte Chemie International Edition
                Angew. Chem. Int. Ed.
                Wiley
                1433-7851
                1521-3773
                November 15 2021
                October 21 2021
                November 15 2021
                : 60
                : 47
                : 24941-24949
                Affiliations
                [1 ]Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Frontiers Science Center for Transformative Molecules School of Chemistry and Chemical Engineering Shanghai Jiao Tong University 800 Dongchuan Road Shanghai 200240 China
                [2 ]College of Chemistry Zhengzhou University Zhengzhou 450052 China
                Article
                10.1002/anie.202111842
                96597adf-54ba-49c6-b329-81a3a4bf4849
                © 2021

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

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

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