Literature DB >> 19231848

Asymmetric oxidation of o-alkylphenols with chiral 2-(o-iodoxyphenyl)-oxazolines.

Jagadish K Boppisetti1, Vladimir B Birman.   

Abstract

A new class of chiral iodine(V) derivatives has been prepared. These compounds have been found to transform ortho-alkylphenols into ortho-quinol Diels-Alder dimers with significant levels of asymmetric induction.

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Year:  2009        PMID： 19231848      PMCID： PMC2779020          DOI： 10.1021/ol8029092

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


  11 in total

1.  Redirecting Secondary Bonds To Control Molecular and Crystal Properties of an Iodosyl- and an Iodylbenzene This work was supported by the donors of The Petroleum Research Fund, administered by the American Chemical Society, and by the Ohio Board of Regents (for financial support of the Ohio Crystallographic Consortium).

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-06-02       Impact factor: 15.336

Review 2.  C(2)-symmetric chiral bis(oxazoline) ligands in asymmetric catalysis.

Authors:  Giovanni Desimoni; Giuseppe Faita; Karl Anker Jørgensen
Journal:  Chem Rev       Date:  2006-09       Impact factor: 60.622

Review 3.  Chemistry of polyvalent iodine.

Authors:  Viktor V Zhdankin; Peter J Stang
Journal:  Chem Rev       Date:  2008-12       Impact factor: 60.622

4.  A chiral hypervalent iodine(III) reagent for enantioselective dearomatization of phenols.

Authors:  Toshifumi Dohi; Akinobu Maruyama; Naoko Takenaga; Kento Senami; Yutaka Minamitsuji; Hiromichi Fujioka; Simon B Caemmerer; Yasuyuki Kita
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Regioselective oxidation of phenols to o-quinones with o-iodoxybenzoic acid (IBX).

Authors:  Derek Magdziak; Andy A Rodriguez; Ryan W Van De Water; Thomas R R Pettus
Journal:  Org Lett       Date:  2002-01-24       Impact factor: 6.005

6.  Esters of 2-iodoxybenzoic acid: hypervalent iodine oxidizing reagents with a pseudobenziodoxole structure.

Authors:  Viktor V Zhdankin; Alexey Y Koposov; Dmitry N Litvinov; Michael J Ferguson; Robert McDonald; Thanh Luu; Rik R Tykwinski
Journal:  J Org Chem       Date:  2005-08-05       Impact factor: 4.354

7.  Synthesis of the azaphilones using copper-mediated enantioselective oxidative dearomatization.

Authors:  Jianglong Zhu; Nicholas P Grigoriadis; Jonathan P Lee; John A Porco
Journal:  J Am Chem Soc       Date:  2005-07-06       Impact factor: 15.419

8.  Efficient access to orthoquinols and their [4 + 2] cyclodimers via SIBX-mediated hydroxylative phenol dearomatization.

Authors:  Nathalie Lebrasseur; Julien Gagnepain; Aurélie Ozanne-Beaudenon; Jean-Michel Léger; Stéphane Quideau
Journal:  J Org Chem       Date:  2007-07-12       Impact factor: 4.354

9.  Enantioselective synthesis of bicyclo[2.2.2]octenones using a copper-mediated oxidative dearomatization/[4 + 2] dimerization cascade.

Authors:  Suwei Dong; Jianglong Zhu; John A Porco
Journal:  J Am Chem Soc       Date:  2008-02-12       Impact factor: 15.419

10.  Experiments on the synthesis of tetracycline. Part 15. Oxidation of phenols and ring A model phenols to o-hydroxy-dienones with benzeneseleninic anhydride.

Authors:  D H Barton; S V Ley; P D Magnus; M N Rosenfeld
Journal:  J Chem Soc Perkin 1       Date:  1977
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  10 in total

1.  Asymmetric oxidative dearomatizations promoted by hypervalent iodine(III) reagents: an opportunity for rational catalyst design?

Authors:  Andrew M Harned
Journal:  Tetrahedron Lett       Date:  2014-08-20       Impact factor: 2.415

2.  Palladium(0)-catalyzed arylative dearomatization of phenols.

Authors:  Sophie Rousseaux; Jorge García-Fortanet; Miguel Angel Del Aguila Sanchez; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2011-05-25       Impact factor: 15.419

3.  Structural basis for selectivity in flavin-dependent monooxygenase-catalyzed oxidative dearomatization.

Authors:  Attabey Rodríguez Benítez; Sara Tweedy; Summer A Baker Dockrey; April L Lukowski; Troy Wymore; Dheeraj Khare; Charles L Brooks; Bruce A Palfey; Janet L Smith; Alison R H Narayan
Journal:  ACS Catal       Date:  2019-03-25       Impact factor: 13.084

Review 4.  Dearomatization strategies in the synthesis of complex natural products.

Authors:  Stéphane P Roche; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

5.  Mechanism and Origins of Chemo- and Stereoselectivities of Aryl Iodide-Catalyzed Asymmetric Difluorinations of β-Substituted Styrenes.

Authors:  Biying Zhou; Moriana K Haj; Eric N Jacobsen; K N Houk; Xiao-Song Xue
Journal:  J Am Chem Soc       Date:  2018-11-05       Impact factor: 15.419

Review 6.  A survey of chiral hypervalent iodine reagents in asymmetric synthesis.

Authors:  Soumen Ghosh; Suman Pradhan; Indranil Chatterjee
Journal:  Beilstein J Org Chem       Date:  2018-05-30       Impact factor: 2.883

7.  2-Iodo-N-isopropyl-5-methoxybenzamide as a highly reactive and environmentally benign catalyst for alcohol oxidation.

Authors:  Takayuki Yakura; Tomoya Fujiwara; Akihiro Yamada; Hisanori Nambu
Journal:  Beilstein J Org Chem       Date:  2018-04-30       Impact factor: 2.883

8.  Thermal stability of N-heterocycle-stabilized iodanes - a systematic investigation.

Authors:  Andreas Boelke; Yulia A Vlasenko; Mekhman S Yusubov; Boris J Nachtsheim; Pavel S Postnikov
Journal:  Beilstein J Org Chem       Date:  2019-09-27       Impact factor: 2.883

9.  Organocatalytic Enantioselective Synthesis of Bicyclo[2.2.2]octenones via Oxaziridinium Catalysed ortho-Hydroxylative Phenol Dearomatization.

Authors:  Tom D D'Arcy; Mark R J Elsegood; Benjamin R Buckley
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-10       Impact factor: 16.823

10.  Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives.

Authors:  Yu Zhang; Yuting Liao; Xiaohua Liu; Xi Xu; Lili Lin; Xiaoming Feng
Journal:  Chem Sci       Date:  2017-07-24       Impact factor: 9.825
  10 in total

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