Literature DB >> 18630916

Pi-stacking effect on levoglucosenone derived internal chiral auxiliaries. A case of complete enantioselectivity inversion on the Diels-Alder reaction.

Ariel M Sarotti1, Israel Fernández, Rolando A Spanevello, Miguel A Sierra, Alejandra G Suárez.   

Abstract

Detailed quantum chemical calculations, experimental evidence, and NMR data rationalize the participation of pi-stacking interaction in the highly asymmetric Diels-Alder reaction using levoglucosenone derived internal chiral auxiliaries, including the appealing effect of inversion of the enantioselectivity by coordination of the substrate with Et 2AlCl.

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Year:  2008        PMID： 18630916     DOI： 10.1021/ol801140g

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


  3 in total

1.  Alternating Ring-Opening Metathesis Polymerization Provides Easy Access to Functional and Fully Degradable Polymers.

Authors:  Francis O Boadi; Jingling Zhang; Xiaoxi Yu; Surita Bhatia; Nicole S Sampson
Journal:  Macromolecules       Date:  2020-07-16       Impact factor: 5.985

2.  Experimental and theoretical insights in the alkene-arene intramolecular π-stacking interaction.

Authors:  Valeria Corne; Ariel M Sarotti; Carmen Ramirez de Arellano; Rolando A Spanevello; Alejandra G Suárez
Journal:  Beilstein J Org Chem       Date:  2016-07-28       Impact factor: 2.883

3.  Understand the Specific Regio- and Enantioselectivity of Fluostatin Conjugation in the Post-Biosynthesis.

Authors:  Yuanqi Wang; Changsheng Zhang; Yi-Lei Zhao; Rosalinda Zhao; Kendall N Houk
Journal:  Biomolecules       Date:  2020-05-26
  3 in total

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