Literature DB >> 28573860

Enantioselective Iridium-Catalyzed Allylic Cyclizations.

Michael A Schafroth1, Stephan M Rummelt1, David Sarlah1, Erick M Carreira1.   

Abstract

A method for the enantioselective synthesis of carbo- and heterocyclic ring systems enabled through the combination of Lewis acid activation and iridium-catalyzed allylic substitution is described. The reaction proceeds with branched, allylic alcohols and carbon nucleophiles as well as heteronucleophiles to give a diverse set of ring systems in good yields and with high enantioselectivities. The utility of the method is highlighted by the asymmetric syntheses of erythrococcamides A and B.

Entities:  

Year:  2017        PMID: 28573860     DOI: 10.1021/acs.orglett.7b01346

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

1.  Regio- and Enantioselective Iridium-Catalyzed N-Allylation of Indoles and Related Azoles with Racemic Branched Alkyl-Substituted Allylic Acetates.

Authors:  Seung Wook Kim; Tabitha T Schempp; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-06       Impact factor: 15.336

2.  Stereodivergent Allylation of Azaaryl Acetamides and Acetates by Synergistic Iridium and Copper Catalysis.

Authors:  Xingyu Jiang; Philip Boehm; John F Hartwig
Journal:  J Am Chem Soc       Date:  2018-01-17       Impact factor: 15.419

3.  Rhodium-catalyzed asymmetric intramolecular hydroarylation of allenes: access to functionalized benzocycles.

Authors:  Dino Berthold; Johannes Klett; Bernhard Breit
Journal:  Chem Sci       Date:  2019-09-10       Impact factor: 9.825

4.  Palladium-catalyzed tandem allylic substitution/cyclization and cascade hydrosilylated reduction: the influence of reaction parameters and hydrosilanes on the stereoselectivity.

Authors:  Peng-Wei Long; Jian-Xing Xu; Xing-Feng Bai; Zheng Xu; Zhan-Jiang Zheng; Ke-Fang Yang; Li Li; Li-Wen Xu
Journal:  RSC Adv       Date:  2018-06-22       Impact factor: 3.361

5.  Iridium-Catalyzed Enantioselective Intermolecular Indole C2-Allylation.

Authors:  James A Rossi-Ashton; Aimee K Clarke; James R Donald; Chao Zheng; Richard J K Taylor; William P Unsworth; Shu-Li You
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-11       Impact factor: 15.336

  5 in total

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