For Publishers
DiscoveryMetadataPeer reviewHostingPublishing
For Researchers
JoinPublishReviewCollect
Register
Blog
About
Search
Advanced search
My ScienceOpen
Search
For Publishers
For Researchers
Blog
About
9
views
39
references
 Top references
cited by
1
    
0 reviews
 Review
0
comments
 Comment
0
recommends
+1 Recommend
0 collections
    0
    shares
      33
      similar
       All similar
      • Record: found
      • Abstract: found
      • Article: found
      Is Open Access

      Enantioselective Allylation of Stereogenic Nitrogen Centers

      rapid-communication
      Author(s): , ,
      Publication date (Electronic):
      Journal: Organic Letters
      Publisher: American Chemical Society

      Read this article at

      ScienceOpenPublisherPMC
          There is no author summary for this article yet. Authors can add summaries to their articles on ScienceOpen to make them more accessible to a non-specialist audience.

          Abstract

          Most tertiary amines with a stereogenic nitrogen center undergo rapid racemization at room temperature. Consequently, the quaternization of amines under dynamic kinetic resolution seems feasible. N-Methyl tetrahydroisoquinolines are converted into configurationally stable ammonium ions by Pd-catalyzed allylic alkylation. The optimization of conditions and the evaluation of the substrate scope enabled high conversions and an enantiomeric ratio of up to 10:90. We report here the first examples for the enantioselective catalytic synthesis of chiral ammonium ions.

          Related collections

          Most cited references39

          • Record: found
          • Abstract: found
          • Article: not found

          Enantioselective remote C–H activation directed by a chiral cation

          Georgi Genov, James L. Douthwaite, Antti S. K. Lahdenperä … (2020)
          Chiral cations have been used extensively as organocatalysts, but their application to rendering transition metal–catalyzed processes enantioselective remains rare. This is despite the success of the analogous charge-inverted strategy in which cationic metal complexes are paired with chiral anions. We report here a strategy to render a common bipyridine ligand anionic and pair its iridium complexes with a chiral cation derived from quinine. We have applied these ion-paired complexes to long-range asymmetric induction in the desymmetrization of the geminal diaryl motif, located on a carbon or phosphorus center, by enantioselective C–H borylation. In principle, numerous common classes of ligand could likewise be amenable to this approach.
          Article 0 comments Cited 75 times – based on 0 reviews     Review now
            • Record: found
            • Abstract: not found
            • Article: not found

            Efficient catalytic asymmetric alkylations. 1. Enantioselective synthesis of (+)-indacrinone via chiral phase-transfer catalysis

            Ulf H Dolling, Paul Davis, Edward Grabowski (1984)
            Article 0 comments Cited 75 times – based on 0 reviews     Review now
              • Record: found
              • Abstract: found
              • Article: not found

              Ion-paired chiral ligands for asymmetric palladium catalysis

              Kohsuke Ohmatsu, Mitsunori Ito, Tomoatsu Kunieda … (2012)
              Conventional chiral ligands rely on the use of a covalently constructed, single chiral molecule embedded with coordinative functional groups. Here, we report a new strategy for the design of a chiral ligand for asymmetric transition-metal catalysis; our approach is based on the development of an achiral cationic ammonium-phosphine hybrid ligand paired with a chiral binaphtholate anion. This ion-paired chiral ligand imparts a remarkable stereocontrolling ability to its palladium complex, which catalyses a highly enantioselective allylic alkylation of α-nitrocarboxylates. By exploiting the possible combinations of the achiral onium entities with suitable coordinative functionalities and readily available chiral acids, this approach should contribute to the development of a broad range of metal-catalysed, stereoselective chemical transformations.
              Article 0 comments Cited 39 times – based on 0 reviews     Review now
                All references

                Author and article information

                Journal
                Journal ID (nlm-ta): Org Lett
                Journal ID (iso-abbrev): Org Lett
                Journal ID (publisher-id): ol
                Journal ID (coden): orlef7
                Title: Organic Letters
                Publisher: American Chemical Society
                ISSN (Print): 1523-7060
                ISSN (Electronic): 1523-7052
                Publication date (Electronic): 07 March 2023
                Publication date Collection: 17 March 2023
                Volume: 25
                Issue: 10
                Pages: 1649-1654
                Affiliations
                [1]Department of Chemistry, University of Basel , Mattenstrasse 22, 4058 Basel, Switzerland
                Author notes
                Author information
                https://orcid.org/0000-0002-3631-5210
                https://orcid.org/0000-0002-7828-423X
                Article
                DOI: 10.1021/acs.orglett.3c00195
                PMC ID: 10028698
                PubMed ID: 36881477
                SO-VID: 2949e08e-43c1-4fcf-9a1f-9d78338edbda
                Copyright © © 2023 The Authors. Published by American Chemical Society
                License:

                Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained ( https://creativecommons.org/licenses/by/4.0/).

                History
                Date received : 18 January 2023
                Categories
                Subject: Letter
                Custom metadata
                document-id-old-9 ol3c00195
                document-id-new-14 ol3c00195
                ccc-price

                ScienceOpen disciplines: Organic & Biomolecular chemistry
                Data availability:
                ScienceOpen disciplines: Organic & Biomolecular chemistry

                Comments

                Comment on this article

                Related Documents Log