Literature DB >> 11982351

Aromatic 4-tetrahydropyranyl and 4-quinuclidinyl cations. Linking Prins with Cope and Grob.

Roger W Alder1, Jeremy N Harvey, Mark T Oakley.   

Abstract

The chair 4-tetrahydropyranyl cation and the 4-quinuclidinyl cation are shown to be energy minima and to be delocalized, with exceptionally long CH2CH2 bonds, according to B3LYP/6-31G* calculations; the implications for Prins cyclizations, Cope rearrangements, and Grob fragmentations are discussed.

Entities:  

Year:  2002        PMID: 11982351     DOI: 10.1021/ja025902+

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


  17 in total

1.  Racemization in Prins cyclization reactions.

Authors:  Ramesh Jasti; Scott D Rychnovsky
Journal:  J Am Chem Soc       Date:  2006-10-18       Impact factor: 15.419

2.  Pyranone natural products as inspirations for catalytic reaction discovery and development.

Authors:  Benjamin R McDonald; Karl A Scheidt
Journal:  Acc Chem Res       Date:  2015-03-06       Impact factor: 22.384

3.  Multifaceted Ion Exchange Resin-Supported Hydrogen Fluoride: A Path to Flow Hydrofluorination.

Authors:  Zhichao Lu; Bhvandip S Bajwa; Otome E Okoromoba; Gerald B Hammond; Bo Xu
Journal:  Green Chem       Date:  2018-12-26       Impact factor: 10.182

4.  Origin of stereocontrol in the construction of the 12-oxatricyclo[6.3.1.0(2,7)]dodecane ring system by Prins-pinacol reactions.

Authors:  Larry E Overman; Paul S Tanis
Journal:  J Org Chem       Date:  2010-01-15       Impact factor: 4.354

5.  Rhenium(VII) catalysis of Prins cyclization reactions.

Authors:  Kwanruthai Tadpetch; Scott D Rychnovsky
Journal:  Org Lett       Date:  2008-09-25       Impact factor: 6.005

6.  Prins fluorination cyclisations: Preparation of 4-fluoro-pyran and -piperidine heterocycles.

Authors:  Guillaume G Launay; Alexandra M Z Slawin; David O'Hagan
Journal:  Beilstein J Org Chem       Date:  2010-04-26       Impact factor: 2.883

7.  Stereoselective synthesis of spirocyclic oxindoles via Prins cyclizations.

Authors:  M Paola Castaldi; Dawn M Troast; John A Porco
Journal:  Org Lett       Date:  2009-08-06       Impact factor: 6.005

8.  Total synthesis of leucascandrolide a: a new application of the Mukaiyama aldol-Prins reaction.

Authors:  Lori J Van Orden; Brian D Patterson; Scott D Rychnovsky
Journal:  J Org Chem       Date:  2007-06-27       Impact factor: 4.354

9.  Mechanistic and computational studies of exocyclic stereocontrol in the synthesis of bryostatin-like cis-2,6-disubstituted 4-alkylidenetetrahydropyrans by Prins cyclization.

Authors:  Yasuyuki Ogawa; Phillip P Painter; Dean J Tantillo; Paul A Wender
Journal:  J Org Chem       Date:  2012-11-07       Impact factor: 4.354

10.  Preparation of Fluorinated Tetrahydropyrans and Piperidines using a New Nucleophilic Fluorination Reagent DMPU/HF.

Authors:  Otome E Okoromoba; Gerald B Hammond; Bo Xu
Journal:  Org Lett       Date:  2015-08-11       Impact factor: 6.005

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