Literature DB >> 30449905

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

Arun K Ghosh1, Jorden Kass1, Daniel R Nicponski1, Chad Keyes1.   

Abstract

We developed a copper(II) triflate-bisphosphine complex catalyzed olefin migration and Prins cyclization which lead to the synthesis of substituted tetrahydropyran derivatives. The protocol is convenient and a variety of substituted tetrahydropyrans were obtained in good to excellent yields with excellent diastereoselectivities.

Entities:  

Keywords:  Prins cyclization; diastereoselective; metal-ligand catalyzed; olefin migration; tetrahydropyrans

Year:  2012        PMID： 30449905      PMCID： PMC6237189          DOI： 10.1055/s-0032-1317495

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN： 0039-7881            Impact factor:   3.157


  18 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.  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

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.  Diverse cyclization catalyzed by In(OTf)3 for the convergent assembly of substituted tetrahydrofurans and tetrahydropyrans.

Authors:  T P Loh; Q Y Hu; K T Tan; H S Cheng
Journal:  Org Lett       Date:  2001-08-23       Impact factor: 6.005

5.  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

6.  Lewis Acid-Promoted Mukaiyama Aldol-Prins (MAP) Cyclizations of Acetals, Ketals, α-Acetoxy Ethers, and Orthoformates.

Authors:  Michael R Gesinski; Lori J Van Orden; Scott D Rychnovsky
Journal:  Synlett       Date:  2008-02-12       Impact factor: 2.454

7.  New Lewis-Acidic Molybdenum(II) and Tungsten(II) Catalysts for Intramolecular Carbonyl Ene and Prins Reactions. Reversal of the Stereoselectivity of Cyclization of Citronellal.

Authors:  Pavel Kocovský; Ghafoor Ahmed; Jirí Srogl; Andrei V. Malkov; John Steele
Journal:  J Org Chem       Date:  1999-04-16       Impact factor: 4.354

8.  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

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

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

10.  Evolution of the Petasis-Ferrier union/rearrangement tactic: construction of architecturally complex natural products possessing the ubiquitous cis-2,6-substituted tetrahydropyran structural element.

Authors:  Amos B Smith; Richard J Fox; Thomas M Razler
Journal:  Acc Chem Res       Date:  2008-05       Impact factor: 22.384
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