Literature DB >> 17458976

Highly stereoselective prins cyclization of (Z)- and (E)-gamma-brominated homoallylic alcohols to 2,4,5,6-tetrasubstituted tetrahydropyrans.

Feng Liu1, Teck-Peng Loh.   

Abstract

An efficient method has been developed to construct 2,6-cis-4,5-dibromo-tetrasubstituted tetrahydropyran (THP) rings with well-controlled stereochemistry in moderate to high yields.

Entities:  

Year:  2007        PMID： 17458976     DOI： 10.1021/ol070506n

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


  6 in total

1.  Diastereoselective, three-component cascade synthesis of tetrahydrofurans and tetrahydropyrans employing the tandem Mukaiyama aldol-lactonization process.

Authors:  T Andrew Mitchell; Cunxiang Zhao; Daniel Romo
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

2.  Synthesis of (-)-okilactomycin by a Prins-type fragment-assembly strategy.

Authors:  Jason M Tenenbaum; William J Morris; Daniel W Custar; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2011-05-10       Impact factor: 15.336

3.  Synthesis of 2,6-disubstituted dihydropyrans via an efficient BiBr(3)-initiated three component, one-pot cascade.

Authors:  Robert J Hinkle; Yajing Lian; Lee C Speight; Heather E Stevenson; Melissa M Sprachman; Lauren A Katkish; M Christa Mattern
Journal:  Tetrahedron       Date:  2009-08-22       Impact factor: 2.457

4.  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

5.  An Enamide-Based Domino Reaction for a Highly Stereoselective Synthesis of Tetrahydropyrans.

Authors:  Philipp Kramer; Jennifer Grimmer; Michael Bolte; Georg Manolikakes
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-07       Impact factor: 15.336

6.  In(III)-TMSBr-Catalyzed Cascade Reaction of Diarylalkynes with Acrylates for the Synthesis of Aryldihydronaphthalene Derivatives.

Authors:  Qiu-Chi Zhang; Wen-Wei Zhang; Liang Shen; Zhi-Liang Shen; Teck-Peng Loh
Journal:  Molecules       Date:  2018-04-23       Impact factor: 4.411
  6 in total

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