Literature DB >> 16671810

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

Ramesh Jasti1, Scott D Rychnovsky.   

Abstract

[reaction: see text] A solvolysis reaction is used to demonstrate that a tetrahydropyranyl cation is a common intermediate for Prins cyclizations, 2-oxonia-Cope rearrangements, and Grob fragmentations of tetrahydropyran rings.

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Year:  2006        PMID： 16671810      PMCID： PMC2487678          DOI： 10.1021/ol0606738

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


  21 in total

1.  Role of 2-oxonia Cope rearrangements in Prins cyclization reactions.

Authors:  S D Rychnovsky; S Marumoto; J J Jaber
Journal:  Org Lett       Date:  2001-11-15       Impact factor: 6.005

2.  General Synthesis of alpha-Acetoxy Ethers from Esters by DIBALH Reduction and Acetylation.

Authors:  Vilas H. Dahanukar; Scott D. Rychnovsky
Journal:  J Org Chem       Date:  1996-11-15       Impact factor: 4.354

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

Authors:  Roger W Alder; Jeremy N Harvey; Mark T Oakley
Journal:  J Am Chem Soc       Date:  2002-05-08       Impact factor: 15.419

4.  Tetrahydropyran rings from a Mukaiyama-Michael cascade reaction.

Authors:  Megan L Bolla; Brian Patterson; Scott D Rychnovsky
Journal:  J Am Chem Soc       Date:  2005-11-23       Impact factor: 15.419

5.  Acid-promoted Prins cyclizations of enol ethers to form tetrahydropyrans.

Authors:  David J Hart; Chad E Bennett
Journal:  Org Lett       Date:  2003-05-01       Impact factor: 6.005

6.  Oxonia-cope prins cyclizations: a facile method for the synthesis of tetrahydropyranones bearing quaternary centers.

Authors:  Jackline E Dalgard; Scott D Rychnovsky
Journal:  J Am Chem Soc       Date:  2004-12-08       Impact factor: 15.419

7.  Stereoselective synthesis of 4-hydroxy-2,3,6-trisubstituted tetrahydropyrans.

Authors:  Conor St J Barry; Stuart R Crosby; John R Harding; Rachael A Hughes; Clare D King; Gregory D Parker; Christine L Willis
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

8.  Stereocontrolled synthesis of linear 22R-homoallylic sterols via a triflic acid-catalyzed 2-oxonia Cope rearrangement.

Authors:  Teck-Peng Loh; Qi-Ying Hu; Li-Ting Ma
Journal:  Org Lett       Date:  2002-07-11       Impact factor: 6.005

9.  Axial-selective prins cyclizations by solvolysis of alpha-bromo ethers.

Authors:  Ramesh Jasti; Justin Vitale; Scott D Rychnovsky
Journal:  J Am Chem Soc       Date:  2004-08-18       Impact factor: 15.419

10.  Syn- and anti-selective Prins cyclizations of delta,epsilon-unsaturated ketones to 1,3-halohydrins with Lewis acids.

Authors:  R Brandon Miles; Chad E Davis; Robert M Coates
Journal:  J Org Chem       Date:  2006-02-17       Impact factor: 4.354
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  8 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.  Bi(OTf)3-, TfOH-, and TMSOTf-mediated, one-pot epoxide rearrangement, addition, and intramolecular silyl-modified Sakurai (ISMS) cascade toward dihydropyrans: comparison of catalysts and role of Bi(OTf)3.

Authors:  R Frederick Lambert; Robert J Hinkle; Stephen E Ammann; Yajing Lian; Jia Liu; Shane E Lewis; Robert D Pike
Journal:  J Org Chem       Date:  2011-10-25       Impact factor: 4.354

Review 4.  Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

Authors:  Amanda C Jones; Jeremy A May; Richmond Sarpong; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-03       Impact factor: 15.336

5.  Atom economical, one-pot, three-reaction cascade to novel tricyclic 2,4-dihydro-1H-benzo[f]isochromenes.

Authors:  Robert J Hinkle; Shane E Lewis
Journal:  Org Lett       Date:  2013-08-01       Impact factor: 6.005

6.  Identification of an Unexpected 2-Oxonia[3,3]sigmatropic Rearrangement/Aldol Pathway in the Formation of Oxacyclic Rings. Total Synthesis of (+)-Aspergillin PZ.

Authors:  Stephen M Canham; Larry E Overman; Paul S Tanis
Journal:  Tetrahedron       Date:  2011-09-19       Impact factor: 2.457

7.  Correlation analysis of the rates of solvolysis of 4-bromopiperidine: a reaction following a Grob fragmentation pathway.

Authors:  Dennis Neil Kevill; Zoon Ha Ryu; Malcolm John D'Souza
Journal:  Eur J Chem       Date:  2017-06-30

8.  Efficient, highly diastereoselective MS 4 Å-promoted one-pot, three-component synthesis of 2,6-disubstituted-4-tosyloxytetrahydropyrans via Prins cyclization.

Authors:  Naseem Ahmed; Naveen Kumar Konduru
Journal:  Beilstein J Org Chem       Date:  2012-02-01       Impact factor: 2.883
  8 in total

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