Literature DB >> 29240280

Enantioselective Iridium-Catalyzed Phthalide Formation through Internal Redox Allylation of Phthalaldehydes.

James M Cabrera1, Johannes Tauber1, Michael J Krische1.   

Abstract

An inside job: Enantioselective phthalide synthesis was achieved through internal redox allylation of o-phthalaldehydes. Oxidative esterification is balanced by reductive carbonyl addition to achieve an overall redox-neutral process. This method enabled formal syntheses of ent-spirolaxine methyl ether and CJ-12,954.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−C Bond Formation; Homogeneous Catalysis; Hydrogen Transfer; Iridium; asymmetric catalysis

Mesh：

Substances：

Year:  2018        PMID： 29240280      PMCID： PMC5777894          DOI： 10.1002/anie.201712015

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  50 in total

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Review 2.  Dehydrogenation as a substrate-activating strategy in homogeneous transition-metal catalysis.

Authors:  Graham E Dobereiner; Robert H Crabtree
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

3.  Hydrogen autotransfer in the N-alkylation of amines and related compounds using alcohols and amines as electrophiles.

Authors:  Gabriela Guillena; Diego J Ramón; Miguel Yus
Journal:  Chem Rev       Date:  2010-03-10       Impact factor: 60.622

4.  Cobalt-catalyzed enantioselective intramolecular hydroacylation of ketones and olefins.

Authors:  Junfeng Yang; Naohiko Yoshikai
Journal:  J Am Chem Soc       Date:  2014-11-20       Impact factor: 15.419

5.  Diastereo- and Enantioselective Iridium Catalyzed Coupling of Vinyl Aziridines with Alcohols: Site-Selective Modification of Unprotected Diols and Synthesis of Substituted Piperidines.

Authors:  Gang Wang; Jana Franke; Chinh Q Ngo; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-06-15       Impact factor: 15.419

6.  Rhodium-catalyzed asymmetric one-pot transesterification and [2 + 2 + 2] cycloaddition leading to enantioenriched 3,3-disubstituted phthalides.

Authors:  Ken Tanaka; Takuya Osaka; Keiichi Noguchi; Masao Hirano
Journal:  Org Lett       Date:  2007-03-06       Impact factor: 6.005

7.  Catalytic enantioselective synthesis of chiral phthalides by efficient reductive cyclization of 2-acylarylcarboxylates under aqueous transfer hydrogenation conditions.

Authors:  Bo Zhang; Ming-Hua Xu; Guo-Qiang Lin
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005

8.  Diastereo- and Enantioselective Iridium Catalyzed Carbonyl (α-Cyclopropyl)allylation via Transfer Hydrogenation.

Authors:  Ryosuke Tsutsumi; Suckchang Hong; Michael J Krische
Journal:  Chemistry       Date:  2015-07-28       Impact factor: 5.236

Review 9.  C-Alkylation of Ketones and Related Compounds by Alcohols: Transition-Metal-Catalyzed Dehydrogenation.

Authors:  Fei Huang; Zhuqing Liu; Zhengkun Yu
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-07       Impact factor: 15.336

10.  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
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  1 in total

1.  From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.

Authors:  Catherine Gazolla Santana; Michael J Krische
Journal:  ACS Catal       Date:  2021-04-22       Impact factor: 13.084
  1 in total

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