Literature DB >> 23819733

A tandem organocatalytic α-chlorination-aldol reaction that proceeds with dynamic kinetic resolution: a powerful tool for carbohydrate synthesis.

Milan Bergeron-Brlek1, Timothy Teoh, Robert Britton.   

Abstract

A tandem, proline-catalyzed α-chlorination/aldol reaction is described that involves a dynamic kinetic resolution of α-chloroaldehyde intermediates. The resulting syn-chlorohydrins are produced with good to excellent diastereoselectivity in high enantiopurity and provide new opportunities for the synthesis of carbohydrates.

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Year:  2013        PMID： 23819733     DOI： 10.1021/ol401370b

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  11 in total

1.  A Chlorine-Atom-Controlled Terminal-Epoxide-Initiated Bicyclization Cascade Enables a Synthesis of the Potent Cytotoxins Haterumaimides J and K.

Authors:  Sharon E Michalak; Sangkil Nam; David M Kwon; David A Horne; Christopher D Vanderwal
Journal:  J Am Chem Soc       Date:  2019-06-03       Impact factor: 15.419

2.  Synthesis of Complex Glycolates by Enantioconvergent Addition Reactions.

Authors:  Samuel L Bartlett; Jeffrey S Johnson
Journal:  Acc Chem Res       Date:  2017-08-17       Impact factor: 22.384

3.  Direct Zinc(II)-Catalyzed Enantioconvergent Additions of Terminal Alkynes to α-Keto Esters.

Authors:  Blane P Zavesky; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-20       Impact factor: 15.336

4.  Synthesis of Complex Tertiary Glycolates by Enantioconvergent Arylation of Stereochemically Labile α-Keto Esters.

Authors:  Samuel L Bartlett; Kimberly M Keiter; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2017-03-02       Impact factor: 15.419

5.  Preparation of 1,5-Dioxaspiro[5.5]undecan-3-one.

Authors:  Robert A Craig; Russell C Smith; Beau P Pritchett; Benzi I Estipona; Brian M Stoltz
Journal:  Organic Synth       Date:  2016

6.  Dynamic kinetic asymmetric transformations of β-stereogenic α-ketoesters by direct aldolization.

Authors:  Michael T Corbett; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-12       Impact factor: 15.336

7.  Direct synthesis of imino-C-nucleoside analogues and other biologically active iminosugars.

Authors:  Milan Bergeron-Brlek; Michael Meanwell; Robert Britton
Journal:  Nat Commun       Date:  2015-04-23       Impact factor: 14.919

8.  Asymmetric synthesis of functionalized cyclohexanes bearing five stereocenters via a one-pot organocatalytic Michael-Michael-1,2-addition sequence.

Authors:  Pankaj Chauhan; Gregor Urbanietz; Gerhard Raabe; Dieter Enders
Journal:  Chem Commun (Camb)       Date:  2014-07-04       Impact factor: 6.222

9.  Structural Snapshots for Mechanism-Based Inactivation of a Glycoside Hydrolase by Cyclopropyl Carbasugars.

Authors:  Christopher Adamson; Robert J Pengelly; Saeideh Shamsi Kazem Abadi; Saswati Chakladar; Jason Draper; Robert Britton; Tracey M Gloster; Andrew J Bennet
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-26       Impact factor: 15.336

10.  Correction to "Enantioconvergent synthesis of functionalized γ-butyrolactones via (3 + 2)-annulation".

Authors:  C Guy Goodman; Morgan M Walker; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2015-03-09       Impact factor: 15.419
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