Literature DB >> 20361794

Chiral phosphoric acid catalyzed addition of dihydropyrans to N-acyl imines: stereocontrolled access to enantioenriched spirocyclic oxazoletetrahydropyrans with three contiguous stereocenters.

Guilong Li1, Matthew J Kaplan, Lukasz Wojtas, Jon C Antilla.   

Abstract

Dihydropyran derivatives readily undergo addition to N-acyl imines in the presence of chiral phosphoric acids. This addition process yields an attractive product that is capable of a tandem oxidative-cyclization via an epoxide intermediate.

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Year:  2010        PMID： 20361794      PMCID： PMC2863994          DOI： 10.1021/ol100378t

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


  22 in total

1.  A powerful Brønsted acid catalyst for the organocatalytic asymmetric transfer hydrogenation of imines.

Authors:  Sebastian Hoffmann; Abdul Majeed Seayad; Benjamin List
Journal:  Angew Chem Int Ed Engl       Date:  2005-12-01       Impact factor: 15.336

2.  Cooperative coexistence: effective interplay of two Brønsted acids in the asymmetric synthesis of isoquinuclidines.

Authors:  Magnus Rueping; Cengiz Azap
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-27       Impact factor: 15.336

3.  Organocatalytic enantioselective Friedel-Crafts reaction of pyrrole derivatives with imines.

Authors:  Guilong Li; Gerald B Rowland; Emily B Rowland; Jon C Antilla
Journal:  Org Lett       Date:  2007-08-30       Impact factor: 6.005

4.  Chiral Brønsted acid-catalyzed enantioselective three-component Povarov reaction.

Authors:  Hua Liu; Guillaume Dagousset; Géraldine Masson; Pascal Retailleau; Jieping Zhu
Journal:  J Am Chem Soc       Date:  2009-04-08       Impact factor: 15.419

5.  Chiral Brønsted acid-catalyzed inverse electron-demand aza Diels-Alder reaction.

Authors:  Takahiko Akiyama; Hisashi Morita; Kohei Fuchibe
Journal:  J Am Chem Soc       Date:  2006-10-11       Impact factor: 15.419

6.  First asymmetric synthesis of a 6-alkoxy-5,6-dihydro-1,3-oxazine: a promising enantioselective route to beta-amido aldehydes

Authors: 
Journal:  Org Lett       Date:  2000-03-09       Impact factor: 6.005

7.  Organocatalytic asymmetric direct alkylation of alpha-diazoester via C-H bond cleavage.

Authors:  Daisuke Uraguchi; Keiichi Sorimachi; Masahiro Terada
Journal:  J Am Chem Soc       Date:  2005-07-06       Impact factor: 15.419

8.  Brønsted acid-catalyzed desymmetrization of meso-aziridines.

Authors:  Emily B Rowland; Gerald B Rowland; Edwin Rivera-Otero; Jon C Antilla
Journal:  J Am Chem Soc       Date:  2007-09-18       Impact factor: 15.419

9.  Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation.

Authors:  Daisuke Uraguchi; Masahiro Terada
Journal:  J Am Chem Soc       Date:  2004-05-05       Impact factor: 15.419

10.  Highly efficient asymmetric trans-selective aziridination of diazoacetamides and N-Boc-imines catalyzed by chiral Brønsted acids.

Authors:  Xiaofei Zeng; Xin Zeng; Zhenjiang Xu; Min Lu; Guofu Zhong
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005
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  3 in total

1.  Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Brønsted acid catalyzed asymmetric allenylboration reactions.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2012-06-25       Impact factor: 15.419

2.  Catalytic Allylic Oxidation of Cyclic Enamides and 3,4-Dihydro-2H-Pyrans by TBHP.

Authors:  Yang Yu; Ranad Humeidi; James R Alleyn; Michael P Doyle
Journal:  J Org Chem       Date:  2017-08-04       Impact factor: 4.354

3.  Enantioselective Michael addition/iminium ion cyclization cascades of tryptamine-derived ureas.

Authors:  Isabelle Aillaud; David M Barber; Amber L Thompson; Darren J Dixon
Journal:  Org Lett       Date:  2013-05-30       Impact factor: 6.005
  3 in total

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