Literature DB >> 22753996

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

Arun K Ghosh1, Daniel R Nicponski, Jorden Kass.   

Abstract

In situ-generated (bis-DPPMB)-Cu(OTf)(2) complex has been examined to catalyze a tandem olefin migration and Prins cyclization of an alkenol with various aldehydes. The reaction proceeded with electron-rich aromatic aldehydes at room temperature and provided functionalized tetrahydropyrans in good yields. An efficient synthesis of the bis-DPPMB ligand has also been described.

Entities:  

Year:  2012        PMID: 22753996      PMCID: PMC3383828          DOI: 10.1016/j.tetlet.2012.04.006

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  8 in total

Review 1.  Total synthesis of marine polycyclic ethers.

Authors:  Tadashi Nakata
Journal:  Chem Rev       Date:  2005-12       Impact factor: 60.622

2.  Racemization in Prins cyclization reactions.

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

3.  Mono-, di-, and triaryl substituted tetrahydropyrans as cyclooxygenase-2 and tumor growth inhibitors. Synthesis and biological evaluation.

Authors:  Palwinder Singh; Atul Bhardwaj
Journal:  J Med Chem       Date:  2010-05-13       Impact factor: 7.446

4.  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

5.  Stereospecific reduction of phosphine oxides to phosphines by the use of a methylation reagent and lithium aluminum hydride.

Authors:  T Imamoto; S Kikuchi; T Miura; Y Wada
Journal:  Org Lett       Date:  2001-01-11       Impact factor: 6.005

6.  Synthesis and antiproliferative activity of (2R,3R)-disubstituted tetrahydropyrans.

Authors:  Romen Carrillo; Leticia G León; Tomás Martín; Víctor S Martín; José M Padrón
Journal:  Bioorg Med Chem Lett       Date:  2006-09-06       Impact factor: 2.823

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

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

8.  Reduction of tertiary phosphine oxides with DIBAL-H.

Authors:  Carl A Busacca; Ravinder Raju; Nelu Grinberg; Nizar Haddad; Paul James-Jones; Heewon Lee; Jon C Lorenz; Anjan Saha; Chris H Senanayake
Journal:  J Org Chem       Date:  2008-01-16       Impact factor: 4.354

  8 in total
  1 in total

1.  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

  1 in total

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