Literature DB >> 19243137

Multicatalytic synthesis of complex tetrahydrofurans involving bismuth(III) triflate catalyzed intramolecular hydroalkoxylation of unactivated olefins.

Brendan D Kelly1, Julia M Allen, Rachel E Tundel, Tristan H Lambert.   

Abstract

A multicatalytic synthesis of complex tetrahydrofurans has been developed involving a Bi(OTf)(3)-catalyzed nucleophilic addition/hydroalkoxylation sequence. Complex tetrahydrofuranyl products may be formed rapidly in high yield and with good diastereoselectivity. The demonstrated scope of hydroalkoxylation has also been expanded to include substrates bearing useful functional handles including carboxylate ester, olefin, nitrile, and nitro groups.

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Year:  2009        PMID: 19243137     DOI: 10.1021/ol900198r

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


  5 in total

1.  Enamine/Carbene Cascade Catalysis in the Diastereo- and Enantioselective Synthesis of Functionalized Cyclopentanones.

Authors:  Kerem E Ozboya; Tomislav Rovis
Journal:  Chem Sci       Date:  2011-09-01       Impact factor: 9.825

2.  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

3.  Terpene cyclization catalysed inside a self-assembled cavity.

Authors:  Q Zhang; K Tiefenbacher
Journal:  Nat Chem       Date:  2015-02-16       Impact factor: 24.427

4.  α-Hydroxy boron-enabled regioselective access to bifunctional halo-boryl alicyclic ethers and α-halo borons.

Authors:  Lucia Wang; Shengjia Lin; Yawei Zhu; Daniel Ferrante; Timaf Ishak; Yuki Baba; Abhishek Sharma
Journal:  Chem Commun (Camb)       Date:  2021-04-12       Impact factor: 6.222

5.  Boron carboxylate catalysis of homoallylboration.

Authors:  Gabrielle J Dugas; Yu-hong Lam; K N Houk; Isaac J Krauss
Journal:  J Org Chem       Date:  2014-04-24       Impact factor: 4.354

  5 in total

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