Literature DB >> 32392075

Using Neighboring-Group Participation for Acyclic Stereocontrol in Diastereoselective Substitution Reactions of Acetals.

Amanda Ramdular1, K A Woerpel1.   

Abstract

Neighboring-group participation of an ester enabled stereocontrol in substitution reactions of acyclic acetals. The ester group formed a trans-fused dioxolenium ion intermediate, which underwent a substitution reaction at the acetal carbon atom to afford the product with high diastereoselectivity. Neighboring-group participation was confirmed by isolating dioxolane products resulting from nucleophilic addition at C-2 of a 1,3-dioxolenium ion intermediate. Using a pivaloate ester as the participating group in combination with strong nucleophiles produced substitution products with diastereoselectivities of ≥90:10.

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Year:  2020        PMID： 32392075      PMCID： PMC7337985          DOI： 10.1021/acs.orglett.0c01166

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


  20 in total

1.  The influence of neighboring group participation on the hydrolysis of 2-O-substituted methyl glucopyranosides.

Authors:  Mads Heuckendorff; Christian M Pedersen; Mikael Bols
Journal:  Org Lett       Date:  2011-10-18       Impact factor: 6.005

2.  On the nitrile effect in L-rhamnopyranosylation.

Authors:  David Crich; Mitesh Patel
Journal:  Carbohydr Res       Date:  2006-04-27       Impact factor: 2.104

3.  Participation of alkoxy groups in reactions of acetals: violation of the reactivity/selectivity principle in a Curtin-Hammett kinetic scenario.

Authors:  Angie Garcia; Jillian R Sanzone; K A Woerpel
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-19       Impact factor: 15.336

4.  Synthesis of N-glycosides. An alternative approach based on diastereoselective base coupling and S(N)2 cyclization.

Authors:  Yvan Guindon; Marc Gagnon; Isabelle Thumin; Daniel Chapdelaine; Grace Jung; Brigitte Guérin
Journal:  Org Lett       Date:  2002-01-24       Impact factor: 6.005

5.  A stereoselective approach to nucleosides and 4'-thioanalogues from acyclic precursors.

Authors:  Daniel Chapdelaine; Benoit Cardinal-David; Michel Prévost; Marc Gagnon; Isabelle Thumin; Yvan Guindon
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419

6.  Orthoesters versus 2-O-acyl glycosides as glycosyl donors: theorectical and experimental studies.

Authors:  Bert Fraser-Reid; Stefan Grimme; Manuel Piacenza; Mateuz Mach; Urs Schlueter
Journal:  Chemistry       Date:  2003-10-06       Impact factor: 5.236

7.  Does neighboring group participation by non-vicinal esters play a role in glycosylation reactions? Effective probes for the detection of bridging intermediates.

Authors:  David Crich; Tianshun Hu; Feng Cai
Journal:  J Org Chem       Date:  2008-10-22       Impact factor: 4.354

8.  Studies on the Lewis acid mediated cleavage of alpha-aminoacetals: synthesis of novel 1,2-aminoethers, and evidence for alpha-alkoxy aziridinium ion intermediates.

Authors:  Mark A Graham; Alan H Wadsworth; Abdul Zahid; Christopher M Rayner
Journal:  Org Biomol Chem       Date:  2003-03-07       Impact factor: 3.876

9.  Stereocontrolled 1,2-cis glycosylation as the driving force of progress in synthetic carbohydrate chemistry.

Authors:  Swati S Nigudkar; Alexei V Demchenko
Journal:  Chem Sci       Date:  2015-05-01       Impact factor: 9.825

10.  Characterization of glycosyl dioxolenium ions and their role in glycosylation reactions.

Authors:  Thomas Hansen; Hidde Elferink; Jacob M A van Hengst; Kas J Houthuijs; Wouter A Remmerswaal; Alexandra Kromm; Giel Berden; Stefan van der Vorm; Anouk M Rijs; Hermen S Overkleeft; Dmitri V Filippov; Floris P J T Rutjes; Gijsbert A van der Marel; Jonathan Martens; Jos Oomens; Jeroen D C Codée; Thomas J Boltje
Journal:  Nat Commun       Date:  2020-05-29       Impact factor: 14.919
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