Literature DB >> 24025122

Single-operation deracemization of 3H-indolines and tetrahydroquinolines enabled by phase separation.

Aaron D Lackner1, Andrew V Samant, F Dean Toste.   

Abstract

The single-operation deracemization of 3H indolines and tetrahydroquinolines is described. An asymmetric redox approach was employed, in which a phosphoric acid catalyst, oxidant, and reductant are present in the reaction mixture. The simultaneous presence of both oxidant and reductant was enabled by phase separation and resulted in the isolation of highly enantioenriched starting materials in high yields.

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Year:  2013        PMID: 24025122      PMCID: PMC3827023          DOI: 10.1021/ja4082827

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  39 in total

1.  Non-sequential processes for the transformation of a racemate into a single stereoisomeric product: proposal for stereochemical classification.

Authors:  K Faber
Journal:  Chemistry       Date:  2001-12-03       Impact factor: 5.236

2.  Asymmetric electrophilic fluorination using an anionic chiral phase-transfer catalyst.

Authors:  Vivek Rauniyar; Aaron D Lackner; Gregory L Hamilton; F Dean Toste
Journal:  Science       Date:  2011-12-23       Impact factor: 47.728

3.  A powerful Brønsted acid catalyst for the organocatalytic asymmetric transfer hydrogenation of imines.

Authors:  Sebastian Hoffmann; Abdul Majeed Seayad; Benjamin List
Journal:  Angew Chem Int Ed Engl       Date:  2005-12-01       Impact factor: 15.336

4.  Chemoenzymatic dynamic kinetic resolution of primary amines.

Authors:  Jens Paetzold; Jan E Bäckvall
Journal:  J Am Chem Soc       Date:  2005-12-21       Impact factor: 15.419

5.  Optical resolution methods.

Authors:  Elemér Fogassy; Mihály Nógrádi; Dávid Kozma; Gabriella Egri; Emese Pálovics; Violetta Kiss
Journal:  Org Biomol Chem       Date:  2006-07-07       Impact factor: 3.876

6.  Cooperative coexistence: effective interplay of two Brønsted acids in the asymmetric synthesis of isoquinuclidines.

Authors:  Magnus Rueping; Cengiz Azap
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-27       Impact factor: 15.336

7.  A doubly axially chiral phosphoric acid catalyst for the asymmetric tandem oxyfluorination of enamides.

Authors:  Takashi Honjo; Robert J Phipps; Vivek Rauniyar; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-29       Impact factor: 15.336

8.  Asymmetric counteranion-directed catalysis: concept, definition, and applications.

Authors:  Manuel Mahlau; Benjamin List
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-28       Impact factor: 15.336

9.  Enantioselective halocyclization using reagents tailored for chiral anion phase-transfer catalysis.

Authors:  Yi-Ming Wang; Jeffrey Wu; Christina Hoong; Vivek Rauniyar; F Dean Toste
Journal:  J Am Chem Soc       Date:  2012-07-25       Impact factor: 15.419

10.  Ruthenium-catalyzed sequential reactions: deracemization of secondary benzylic alcohols.

Authors:  Yusuke Shimada; Yoshihiro Miyake; Hiroshi Matsuzawa; Yoshiaki Nishibayashi
Journal:  Chem Asian J       Date:  2007-03-05
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  15 in total

1.  Enantioselective 1,1-arylborylation of alkenes: merging chiral anion phase transfer with Pd catalysis.

Authors:  Hosea M Nelson; Brett D Williams; Javier Miró; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-02-27       Impact factor: 15.419

2.  A Redox Strategy for Light-Driven, Out-of-Equilibrium Isomerizations and Application to Catalytic C-C Bond Cleavage Reactions.

Authors:  Eisuke Ota; Huaiju Wang; Nils Lennart Frye; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2019-01-15       Impact factor: 15.419

3.  Self-Assembly of a Library of Polyborate Chiral Anions for Asymmetric Catalytic Quinoline Reduction.

Authors:  Aman A Desai; Yong Guan; Aaron L Odom; Supriyo Majumder; William D Wulff
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

4.  Biomimetic Approach to the Catalytic Enantioselective Synthesis of Flavonoids.

Authors:  Zhenyu Yang; Ying He; F Dean Toste
Journal:  J Am Chem Soc       Date:  2016-07-29       Impact factor: 15.419

5.  Chiral anion phase transfer of aryldiazonium cations: an enantioselective synthesis of C3-diazenated pyrroloindolines.

Authors:  Hosea M Nelson; Solomon H Reisberg; Hunter P Shunatona; Jigar S Patel; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-08       Impact factor: 15.336

6.  Enantiodivergent Fluorination of Allylic Alcohols: Data Set Design Reveals Structural Interplay between Achiral Directing Group and Chiral Anion.

Authors:  Andrew J Neel; Anat Milo; Matthew S Sigman; F Dean Toste
Journal:  J Am Chem Soc       Date:  2016-03-11       Impact factor: 15.419

7.  Multidimensional Correlations in Asymmetric Catalysis through Parameterization of Uncatalyzed Transition States.

Authors:  Manuel Orlandi; F Dean Toste; Matthew S Sigman
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-04       Impact factor: 15.336

8.  Enantioselective Kinetic Resolution/Desymmetrization of Para-Quinols: A Case Study in Boronic-Acid-Directed Phosphoric Acid Catalysis.

Authors:  Banruo Huang; Ying He; Mark D Levin; Jaime A S Coelho; Robert G Bergman; F Dean Toste
Journal:  Adv Synth Catal       Date:  2019-09-06       Impact factor: 5.837

Review 9.  Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

Authors:  Anthony J Metrano; Alex J Chinn; Christopher R Shugrue; Elizabeth A Stone; Byoungmoo Kim; Scott J Miller
Journal:  Chem Rev       Date:  2020-09-24       Impact factor: 60.622

10.  Light-driven deracemization enabled by excited-state electron transfer.

Authors:  Nick Y Shin; Jonathan M Ryss; Xin Zhang; Scott J Miller; Robert R Knowles
Journal:  Science       Date:  2019-10-18       Impact factor: 47.728

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