Literature DB >> 14510570

A versatile indium trichloride mediated Prins-type reaction to unsaturated heterocycles.

Adrian P Dobbs1, Sebastien J J Guesné, Sasa Martinović, Simon J Coles, Michael B Hursthouse.   

Abstract

A versatile and high-yielding indium trichloride mediated cyclization reaction of silylated homoallylic alcohols, thiols, or amines with aldehydes or epoxides is described as a rapid route to a range of unsaturated heterocycles. The excellent diastereoselectivity observed offers a method of wide scope and generality.

Entities:  

Year:  2003        PMID： 14510570     DOI： 10.1021/jo034981k

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  9 in total

1.  Synthesis of sulfur-containing heterocycles through oxidative carbon-hydrogen bond functionalization.

Authors:  Yubo Cui; Paul E Floreancig
Journal:  Org Lett       Date:  2012-03-15       Impact factor: 6.005

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.  Synthesis and Properties of Disulfide-Bond Containing Eight-Membered Rings.

Authors:  Erik L Ruggles; Robert J Hondal
Journal:  Tetrahedron Lett       Date:  2006-06-19       Impact factor: 2.415

4.  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

5.  Prins fluorination cyclisations: Preparation of 4-fluoro-pyran and -piperidine heterocycles.

Authors:  Guillaume G Launay; Alexandra M Z Slawin; David O'Hagan
Journal:  Beilstein J Org Chem       Date:  2010-04-26       Impact factor: 2.883

6.  Synthesis, Redox Properties, and Conformational Analysis of Vicinal Disulfide Ring Mimics.

Authors:  Erik L Ruggles; P Bruce Deker; Robert J Hondal
Journal:  Tetrahedron       Date:  2009-02-14       Impact factor: 2.457

7.  Synthesis of Tetrahydroazepines through Silyl Aza-Prins Cyclization Mediated by Iron(III) Salts.

Authors:  Victoria Sinka; Israel Fernández; Juan I Padrón
Journal:  J Org Chem       Date:  2022-08-17       Impact factor: 4.198

8.  The use of silicon-based tethers for the Pauson-Khand reaction.

Authors:  Adrian P Dobbs; Ian J Miller; Sasa Martinović
Journal:  Beilstein J Org Chem       Date:  2007-07-06       Impact factor: 2.883

Review 9.  InCl3: A Versatile Catalyst for Synthesizing a Broad Spectrum of Heterocycles.

Authors:  Sanjit K Mahato; Chiranjit Acharya; Kevin W Wellington; Pinaki Bhattacharjee; Parasuraman Jaisankar
Journal:  ACS Omega       Date:  2020-02-06
  9 in total

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