Literature DB >> 28039892

Enantioselective Synthesis of Oxetanes Bearing All-Carbon Quaternary Stereocenters via Iridium-Catalyzed C-C Bond-Forming Transfer Hydrogenation.

Yi-An Guo1, Wonchul Lee1, Michael J Krische1.   

Abstract

Oxetanes bearing all-carbon quaternary stereocenters are readily prepared through the iridium-catalyzed anti-diastereo- and enantioselective C-C coupling of primary alcohols and isoprene oxide. Based on this methodology, an oxetane containing analogue of haloperidol was prepared. A related azetidine formation is also described.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  enantioselectivity; iridium; oxetane; quaternary center; transfer hydrogenation

Year:  2017        PMID： 28039892      PMCID： PMC5391976          DOI： 10.1002/chem.201606046

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  20 in total

Review 1.  Mitigating heterocycle metabolism in drug discovery.

Authors:  David J St Jean; Christopher Fotsch
Journal:  J Med Chem       Date:  2012-05-07       Impact factor: 7.446

Review 2.  Oxetanes as versatile elements in drug discovery and synthesis.

Authors:  Johannes A Burkhard; Georg Wuitschik; Mark Rogers-Evans; Klaus Müller; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-22       Impact factor: 15.336

Review 3.  Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry.

Authors:  James A Bull; Rosemary A Croft; Owen A Davis; Robert Doran; Kate F Morgan
Journal:  Chem Rev       Date:  2016-09-15       Impact factor: 60.622

4.  Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective Methods.

Authors:  Abbas Hassan; Michael J Krische
Journal:  Org Process Res Dev       Date:  2011-11-18       Impact factor: 3.317

5.  The consolidation of neuroleptic therapy: Janssen, the discovery of haloperidol and its introduction into clinical practice.

Authors:  Francisco López-Muñoz; Cecilio Alamo
Journal:  Brain Res Bull       Date:  2009-01-30       Impact factor: 4.077

6.  [The discovery of haloperidol].

Authors:  B Granger
Journal:  Encephale       Date:  1999 Jan-Feb       Impact factor: 1.291

7.  Recent Applications of Oxetanes in the Synthesis of Heterocyclic Compounds.

Authors:  Christian A Malapit; Amy R Howell
Journal:  J Org Chem       Date:  2015-08-19       Impact factor: 4.354

8.  Introduction of vinyl and hydroxymethyl functionalities at C-4 of glucose-derived substrates: synthesis of spirocyclic, bicyclic, and tricyclic nucleosides.

Authors:  Joy Krishna Maity; Ramprasad Ghosh; Michael G B Drew; Basudeb Achari; Sukhendu B Mandal
Journal:  J Org Chem       Date:  2008-04-24       Impact factor: 4.354

9.  Redox-triggered C-C coupling of alcohols and vinyl epoxides: diastereo- and enantioselective formation of all-carbon quaternary centers via tert-(hydroxy)-prenylation.

Authors:  Jiajie Feng; Victoria J Garza; Michael J Krische
Journal:  J Am Chem Soc       Date:  2014-06-10       Impact factor: 15.419

Review 10.  Oxetane synthesis through the Paternò-Büchi reaction.

Authors:  Maurizio D'Auria; Rocco Racioppi
Journal:  Molecules       Date:  2013-09-16       Impact factor: 4.411
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  9 in total

1.  Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis.

Authors:  Jiajie Feng; Michael Holmes; Michael J Krische
Journal:  Chem Rev       Date:  2017-09-14       Impact factor: 60.622

2.  Nickel-Catalyzed Cross-Coupling of Vinyl Dioxanones to Form Enantiomerically Enriched Cyclopropanes.

Authors:  Yi-An Guo; Tao Liang; Seung Wook Kim; Hongde Xiao; Michael J Krische
Journal:  J Am Chem Soc       Date:  2017-05-10       Impact factor: 15.419

3.  Catalytic Nucleophilic Allylation Driven by the Water-Gas Shift Reaction.

Authors:  Scott E Denmark; Zachery D Matesich; Son T Nguyen; Selena Milicevic Sephton
Journal:  J Org Chem       Date:  2017-12-08       Impact factor: 4.354

Review 4.  Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis.

Authors:  Rosalie S Doerksen; Cole C Meyer; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-26       Impact factor: 15.336

5.  Enantioselective Formation of CF3-Bearing All-Carbon Quaternary Stereocenters via C-H Functionalization of Methanol: Iridium Catalyzed Allene Hydrohydroxymethylation.

Authors:  Michael Holmes; Khoa D Nguyen; Leyah A Schwartz; Tom Luong; Michael J Krische
Journal:  J Am Chem Soc       Date:  2017-06-12       Impact factor: 15.419

6.  Cyclometalated Iridium-PhanePhos Complexes Are Active Catalysts in Enantioselective Allene-Fluoral Reductive Coupling and Related Alcohol-Mediated Carbonyl Additions That Form Acyclic Quaternary Carbon Stereocenters.

Authors:  Leyah A Schwartz; Michael Holmes; Gilmar A Brito; Théo P Gonçalves; Jeffery Richardson; J Craig Ruble; Kuo-Wei Huang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-01-25       Impact factor: 15.419

7.  Ethanol: Unlocking an Abundant Renewable C2 -Feedstock for Catalytic Enantioselective C-C Coupling.

Authors:  Cole C Meyer; Nicholas P Stafford; Melinda J Cheng; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2021-03-30       Impact factor: 15.336

Review 8.  An Overview of Saturated Cyclic Ethers: Biological Profiles and Synthetic Strategies.

Authors:  Qili Lu; Dipesh S Harmalkar; Yongseok Choi; Kyeong Lee
Journal:  Molecules       Date:  2019-10-21       Impact factor: 4.411

9.  Enantioselective Total Synthesis of Andrographolide and 14-Hydroxy-Colladonin: Carbonyl Reductive Coupling and trans-Decalin Formation by Hydrogen Transfer.

Authors:  Lin Yang; Thomas Wurm; Binit Sharma Poudel; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2020-10-15       Impact factor: 15.336
  9 in total

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