Literature DB >> 21739552

Scaffolding catalysts: highly enantioselective desymmetrization reactions.

Xixi Sun1, Amanda D Worthy, Kian L Tan.   

Abstract

Ex-changing places: a highly enantioselective desymmetrization of 1,2-diols has been developed in which the catalyst utilizes reversible covalent bonding to the substrate to achieve both high selectivity and rate acceleration (see scheme, PMP=pentalmethylpiperidine, TBS=tert-butyldimethylsilyl). Induced intramolecularity is responsible for the enhanced rate, thus allowing the reaction to be performed at room temperature.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2011        PMID： 21739552      PMCID： PMC3366164          DOI： 10.1002/anie.201103470

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


  32 in total

1.  Discovery of a catalytic asymmetric phosphorylation through selection of a minimal kinase mimic: a concise total synthesis of D-myo-inositol-1-phosphate.

Authors:  B R Sculimbrene; S J Miller
Journal:  J Am Chem Soc       Date:  2001-10-17       Impact factor: 15.419

2.  3,4,5-Trifluorobenzeneboronic Acid as an Extremely Active Amidation Catalyst.

Authors:  Kazuaki Ishihara; Suguru Ohara; Hisashi Yamamoto
Journal:  J Org Chem       Date:  1996-06-26       Impact factor: 4.354

3.  Asymmetric Si-O coupling of alcohols.

Authors:  Andreas Weickgenannt; Marius Mewald; Martin Oestreich
Journal:  Org Biomol Chem       Date:  2010-02-03       Impact factor: 3.876

4.  Direct and waste-free amidations and cycloadditions by organocatalytic activation of carboxylic acids at room temperature.

Authors:  Raed M Al-Zoubi; Olivier Marion; Dennis G Hall
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 5.  Asymmetric enamine catalysis.

Authors:  Santanu Mukherjee; Jung Woon Yang; Sebastian Hoffmann; Benjamin List
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

6.  Asymmetric aminocatalysis--gold rush in organic chemistry.

Authors:  Paolo Melchiorre; Mauro Marigo; Armando Carlone; Giuseppe Bartoli
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

7.  Catalytic scaffolding ligands: an efficient strategy for directing reactions.

Authors:  Thomas E Lightburn; Michael T Dombrowski; Kian L Tan
Journal:  J Am Chem Soc       Date:  2008-06-25       Impact factor: 15.419

8.  Application of a chiral scaffolding ligand in catalytic enantioselective hydroformylation.

Authors:  Amanda D Worthy; Candice L Joe; Thomas E Lightburn; Kian L Tan
Journal:  J Am Chem Soc       Date:  2010-10-27       Impact factor: 15.419

9.  Enantioselective silyl protection of alcohols catalysed by an amino-acid-based small molecule.

Authors:  Yu Zhao; Jason Rodrigo; Amir H Hoveyda; Marc L Snapper
Journal:  Nature       Date:  2006-09-07       Impact factor: 49.962

10.  Enantioselective sulfonylation reactions mediated by a tetrapeptide catalyst.

Authors:  Kristin Williams Fiori; Angela L A Puchlopek; Scott J Miller
Journal:  Nat Chem       Date:  2009-11       Impact factor: 24.427
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  14 in total

1.  Catalysis: Temporary intramolecularity.

Authors:  Kian L Tan
Journal:  Nat Chem       Date:  2012-03-22       Impact factor: 24.427

2.  Site-selective reactions: Exploiting intramolecularity.

Authors:  André M Beauchemin
Journal:  Nat Chem       Date:  2013-09       Impact factor: 24.427

3.  Practical silyl protection of ribonucleosides.

Authors:  Thomas P Blaisdell; Sunggi Lee; Pinar Kasaplar; Xixi Sun; Kian L Tan
Journal:  Org Lett       Date:  2013-09-03       Impact factor: 6.005

4.  Scaffolding Catalysis: Expanding the Repertoire of Bifunctional Catalysts.

Authors:  Kian L Tan; Xixi Sun; Amanda D Worthy
Journal:  Synlett       Date:  2012-02-01       Impact factor: 2.454

5.  Total Synthesis of (±)-Phyllantidine: Development and Mechanistic Evaluation of a Ring Expansion for Installation of Embedded Nitrogen-Oxygen Bonds.

Authors:  Kyle M Lambert; Joshua B Cox; Lin Liu; Amy C Jackson; Sam Yruegas; Kenneth B Wiberg; John L Wood
Journal:  Angew Chem Int Ed Engl       Date:  2020-05-08       Impact factor: 15.336

6.  Site-Selective and Stereoselective O-Alkylation of Glycosides by Rh(II)-Catalyzed Carbenoid Insertion.

Authors:  Jicheng Wu; Xiaolei Li; Xiaotian Qi; Xiyan Duan; Weston L Cracraft; Ilia A Guzei; Peng Liu; Weiping Tang
Journal:  J Am Chem Soc       Date:  2019-12-03       Impact factor: 15.419

7.  Site-selective catalysis: toward a regiodivergent resolution of 1,2-diols.

Authors:  Amanda D Worthy; Xixi Sun; Kian L Tan
Journal:  J Am Chem Soc       Date:  2012-04-19       Impact factor: 15.419

Review 8.  Synthesis of 5'-O-DMT-2'-O-TBS Mononucleosides Using an Organic Catalyst.

Authors:  Sunggi Lee; Thomas P Blaisdell; Pinar Kasaplar; Xixi Sun; Kian L Tan
Journal:  Curr Protoc Nucleic Acid Chem       Date:  2014-06-24

9.  Resolution of terminal 1,2-diols via silyl transfer.

Authors:  Xixi Sun; Amanda D Worthy; Kian L Tan
Journal:  J Org Chem       Date:  2013-10-02       Impact factor: 4.354

10.  The efficient desymmetrization of glycerol using scaffolding catalysis.

Authors:  Zachary X Giustra; Kian L Tan
Journal:  Chem Commun (Camb)       Date:  2013-05-14       Impact factor: 6.222
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