Literature DB >> 23750053

Dearomatization applications of I(III) reagents and some unusual reactivity amongst resorcinol derived cyclohexadienones.

Todd A Wenderski1, Christophe Hoarau, Lupe Mejorado, Thomas R R Pettus.   

Abstract

The oxidative dearomatization of resorcinol derivatives, which are outfitted with a lactic acid derived chiral tether, and mitigated by hypervalent iodine derivatives of PhIO, affords stable chiral cyclohexadienones as useful building blocks for the construction of many highly functionalized chiral six and seven-membered ring systems. Herein, we report a multitude of remarkable and unexpected diastereoselective transformations stemming from these cyclohexadienone adducts.

Entities:  

Keywords:  Cyclohexadienone; Dearomatization; Hypervalent iodine; Lactone; Vinylogous ester

Year:  2010        PMID： 23750053      PMCID： PMC3676312          DOI： 10.1016/j.tet.2010.05.041

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  14 in total

1.  A mild anionic method for generating o-quinone methides: facile preparations of ortho-functionalized phenols.

Authors:  R M Jones; R W Van De Water; C C Lindsey; C Hoarau; T Ung; T R Pettus
Journal:  J Org Chem       Date:  2001-05-18       Impact factor: 4.354

2.  Cyclohexadienone ketals and quinols: four building blocks potentially useful for enantioselective synthesis.

Authors:  D Magdziak; S J Meek; T R R Pettus
Journal:  Chem Rev       Date:  2004-03       Impact factor: 60.622

3.  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

4.  Enantioselective Kita oxidative spirolactonization catalyzed by in situ generated chiral hypervalent iodine(III) species.

Authors:  Muhammet Uyanik; Takeshi Yasui; Kazuaki Ishihara
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-15       Impact factor: 15.336

5.  Total synthesis of (+)-rishirilide B: development and application of general processes for enantioselective oxidative dearomatization of resorcinol derivatives.

Authors:  Lupe H Mejorado; Thomas R R Pettus
Journal:  J Am Chem Soc       Date:  2006-12-13       Impact factor: 15.419

6.  Synthesis of (+/-)-epoxysorbicillinol using a novel cyclohexa-2,5-dienone with synthetic applications to other sorbicillin derivatives.

Authors:  L H Pettus; R W Van De Water; T R Pettus
Journal:  Org Lett       Date:  2001-03-22       Impact factor: 6.005

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.  Strategies for the Preparation of Differentially Protected ortho-Prenylated Phenols.

Authors:  Christophe Hoarau; Thomas R R Pettus
Journal:  Synlett       Date:  2003       Impact factor: 2.454

9.  Enantioselective total synthesis of all of the known chiral cleroindicins (C-F): clarification among optical rotations and assignments.

Authors:  Todd A Wenderski; Shenlin Huang; Thomas R R Pettus
Journal:  J Org Chem       Date:  2009-06-05       Impact factor: 4.354

10.  Diastereoselective dearomatization of resorcinols directed by a lactic acid tether: unprecedented enantioselective access to p-quinols.

Authors:  Lupe H Mejorado; Christophe Hoarau; Thomas R R Pettus
Journal:  Org Lett       Date:  2004-05-13       Impact factor: 6.005
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  4 in total

1.  A strategy for the late-stage divergent syntheses of scyphostatin analogues.

Authors:  Jacob Y Cha; G Leslie Burnett; Yaodong Huang; Jarrod B Davidson; Thomas R R Pettus
Journal:  J Org Chem       Date:  2011-01-21       Impact factor: 4.354

Review 2.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

3.  Photocatalytic Oxidative Dearomatization of Orcinaldehyde Derivatives.

Authors:  Summer A Baker Dockrey; Alison R H Narayan
Journal:  Org Lett       Date:  2020-04-15       Impact factor: 6.005

4.  Synthesis of highly substituted oxazoles through iodine(III)-mediated reactions of ketones with nitriles.

Authors:  Akio Saito; Nao Hyodo; Yuji Hanzawa
Journal:  Molecules       Date:  2012-09-13       Impact factor: 4.411
  4 in total

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