Literature DB >> 25636054

Resolution of diols via catalytic asymmetric acetalization.

Ji Hye Kim1, Ilija Čorić, Chiara Palumbo, Benjamin List.   

Abstract

A highly enantioselective kinetic resolution of diols via asymmetric acetalization has been achieved using a chiral confined imidodiphosphoric acid catalyst. The reaction is highly efficient for the resolution of tertiary alcohols, giving selectivity factors of up to >300. Remarkably, even in cases where the selectivity factors are only moderate, highly enantioenriched diols are obtained via a stereodivergent resolution to diastereomeric acetals.

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Year:  2015        PMID: 25636054     DOI: 10.1021/ja512481d

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


  11 in total

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Journal:  J Am Chem Soc       Date:  2017-06-19       Impact factor: 15.419

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3.  Studies of Catalyst-Controlled Regioselective Acetalization and Its Application to Single-Pot Synthesis of Differentially Protected Saccharides.

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Journal:  J Am Chem Soc       Date:  2021-10-27       Impact factor: 15.419

4.  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

5.  A Cooperative Hydrogen Bond Donor-Brønsted Acid System for the Enantioselective Synthesis of Tetrahydropyrans.

Authors:  Mark A Maskeri; Matthew J O'Connor; Ashley A Jaworski; Anna V Bay; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2018-11-27       Impact factor: 15.336

6.  Alkylative kinetic resolution of vicinal diols under phase-transfer conditions: a chiral ammonium borinate catalysis.

Authors:  Martin Pawliczek; Takuya Hashimoto; Keiji Maruoka
Journal:  Chem Sci       Date:  2017-12-12       Impact factor: 9.825

7.  Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters.

Authors:  Shen Qu; Samuel M Smith; Víctor Laina-Martín; Rifahath M Neyyappadath; Mark D Greenhalgh; Andrew D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2020-07-16       Impact factor: 15.336

8.  An induced-fit model for asymmetric organocatalytic reactions: a case study of the activation of olefins via chiral Brønsted acid catalysts.

Authors:  Ingolf Harden; Frank Neese; Giovanni Bistoni
Journal:  Chem Sci       Date:  2022-07-04       Impact factor: 9.969

9.  Access to enantioenriched compounds bearing challenging tetrasubstituted stereocenters via kinetic resolution of auxiliary adjacent alcohols.

Authors:  Shengtong Niu; Hao Zhang; Weici Xu; Prasanta Ray Bagdi; Guoxiang Zhang; Jinggong Liu; Shuang Yang; Xinqiang Fang
Journal:  Nat Commun       Date:  2021-06-18       Impact factor: 14.919

10.  Unified Approach to Imidodiphosphate-Type Brønsted Acids with Tunable Confinement and Acidity.

Authors:  Sebastian A Schwengers; Chandra Kanta De; Oleg Grossmann; Joyce A A Grimm; Natascha R Sadlowski; Gabriela G Gerosa; Benjamin List
Journal:  J Am Chem Soc       Date:  2021-09-03       Impact factor: 15.419

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