Literature DB >> 16027925

Probing the mechanism of Prins cyclisations and application to the synthesis of 4-hydroxytetrahydropyrans.

Conor S Barry1, Nick Bushby, John R Harding, Rachael A Hughes, Gregory D Parker, Richard Roe, Christine L Willis.   

Abstract

Trapping intermediates on the Prins cyclisation pathway with carbon-based nucleophiles has given further insight into factors affecting the acid-mediated reactions of homoallylic alcohols with aldehydes, enabling the design of efficient syntheses of 4-hydroxy-2,6-disubstituted tetrahydropyrans.

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Year:  2005        PMID： 16027925     DOI： 10.1039/b504562b

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  7 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.  Solvolysis of a tetrahydropyranyl mesylate: mechanistic implications for the Prins cyclization, 2-oxonia-cope rearrangement, and Grob fragmentation.

Authors:  Ramesh Jasti; Scott D Rychnovsky
Journal:  Org Lett       Date:  2006-05-11       Impact factor: 6.005

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

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

4.  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

5.  Formal synthesis of (-)-kendomycin featuring a Prins-cyclization to construct the macrocycle.

Authors:  Kevin B Bahnck; Scott D Rychnovsky
Journal:  J Am Chem Soc       Date:  2008-09-04       Impact factor: 15.419

6.  Stereoselective synthesis of protected l- and d-dideoxysugars and analogues via Prins cyclisations.

Authors:  Ryan J Beattie; Thomas W Hornsby; Gemma Craig; M Carmen Galan; Christine L Willis
Journal:  Chem Sci       Date:  2016-01-11       Impact factor: 9.825

7.  Carbonylonium ions: the onium ions of the carbonyl group.

Authors:  Daniel Blanco-Ania; Floris P J T Rutjes
Journal:  Beilstein J Org Chem       Date:  2018-10-04       Impact factor: 2.883
  7 in total

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