Literature DB >> 18816133

Rhenium(VII) catalysis of Prins cyclization reactions.

Kwanruthai Tadpetch1, Scott D Rychnovsky.   

Abstract

The rhenium(VII) complex O3ReOSiPh3 is a particularly effective catalyst for Prins cyclizations using aromatic and alpha,beta-unsaturated aldehydes. The reaction conditions are mild, and the highly substituted 4-hydroxytetrahydropyran products are formed stereoselectively. Rhenium(VII) complexes appear to spontaneously form esters with alcohols and to directly activate electron-rich alcohols for solvolysis. Re2O7 and perrhenic acid are equally effective in catalyzing these cyclizations.

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Year:  2008        PMID： 18816133      PMCID： PMC2665917          DOI： 10.1021/ol8019204

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


  22 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.  The first and highly enantioselective crotylation of aldehydes via an allyl-transfer reaction from a chiral crotyl-donor.

Authors:  J Nokami; M Ohga; H Nakamoto; T Matsubara; I Hussain; K Kataoka
Journal:  J Am Chem Soc       Date:  2001-09-19       Impact factor: 15.419

3.  Highly enantioselective Alk-2-enylation of aldehydes through an allyl-transfer reaction.

Authors:  Junzo Nokami; Kenta Nomiyama; Seiji Matsuda; Nobuyuki Imai; Kazuhide Kataoka
Journal:  Angew Chem Int Ed Engl       Date:  2003-03-17       Impact factor: 15.336

4.  Racemization in Prins cyclization reactions.

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

5.  Formal synthesis of (+)-SCH 351448: the Prins cyclization approach.

Authors:  Kok-Ping Chan; Yvonne Hui Ling; Teck-Peng Loh
Journal:  Chem Commun (Camb)       Date:  2007-01-24       Impact factor: 6.222

6.  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

7.  Stereoselectivity and regioselectivity in the segment-coupling Prins cyclization.

Authors:  J J Jaber; K Mitsui; S D Rychnovsky
Journal:  J Org Chem       Date:  2001-06-29       Impact factor: 4.354

8.  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

9.  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

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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  11 in total

1.  Regio- and stereocontrol in rhenium-catalyzed transposition of allylic alcohols.

Authors:  Aaron T Herrmann; Tatsuo Saito; Craig E Stivala; Janine Tom; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2010-05-05       Impact factor: 15.419

2.  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

3.  Cu(II)-catalyzed olefin migration and Prins cyclization: highly diastereoselective synthesis of substituted tetrahydropyrans.

Authors:  Arun K Ghosh; Daniel R Nicponski
Journal:  Org Lett       Date:  2011-07-28       Impact factor: 6.005

4.  A Tandem Olefin Migration and Prins Cyclization Using Cu(OTf)(2)-Bisphosphine Complexes: An Improved Synthesis of Functionalized Tetrahydropyrans.

Authors:  Arun K Ghosh; Daniel R Nicponski; Jorden Kass
Journal:  Tetrahedron Lett       Date:  2012-04-09       Impact factor: 2.415

5.  Diastereoselective Synthesis of Substituted Tetrahydropyrans by Copper(II)-Bisphosphine-Catalyzed Olefin Migration and Prins Cyclization.

Authors:  Arun K Ghosh; Jorden Kass; Daniel R Nicponski; Chad Keyes
Journal:  Synthesis (Stuttg)       Date:  2012-12       Impact factor: 3.157

6.  Symmetric macrocycles by a Prins dimerization and macrocyclization strategy.

Authors:  Michael R Gesinski; Kwanruthai Tadpetch; Scott D Rychnovsky
Journal:  Org Lett       Date:  2009-11-19       Impact factor: 6.005

7.  Cascade approach to stereoselective polycyclic ether formation: epoxides as trapping agents in the transposition of allylic alcohols.

Authors:  Youwei Xie; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-22       Impact factor: 15.336

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

9.  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

10.  Re2O7-catalyzed reaction of hemiacetals and aldehydes with O-, S-, and C-nucleophiles.

Authors:  Wantanee Sittiwong; Michael W Richardson; Charles E Schiaffo; Thomas J Fisher; Patrick H Dussault
Journal:  Beilstein J Org Chem       Date:  2013-07-30       Impact factor: 2.883
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