Literature DB >> 21612204

Palladium(0)-catalyzed arylative dearomatization of phenols.

Sophie Rousseaux1, Jorge García-Fortanet, Miguel Angel Del Aguila Sanchez, Stephen L Buchwald.   

Abstract

The palladium-catalyzed arylative dearomatization of phenols to yield spirocyclohexadienone products in good to excellent yields has been developed. Preliminary results demonstrate that the formation of the spirocyclic all-carbon quaternary center can be accomplished with high levels of enantiocontrol (up to 91% ee).

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Year:  2011        PMID： 21612204      PMCID： PMC3124856          DOI： 10.1021/ja203644q

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  23 in total

1.  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

2.  Pd-catalyzed C3-selective allylation of indoles with allyl alcohols promoted by triethylborane.

Authors:  Masanari Kimura; Makoto Futamata; Ryutaro Mukai; Yoshinao Tamaru
Journal:  J Am Chem Soc       Date:  2005-04-06       Impact factor: 15.419

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.  Iridium-catalyzed intramolecular asymmetric allylic dearomatization of phenols.

Authors:  Qing-Feng Wu; Wen-Bo Liu; Chun-Xiang Zhuo; Zi-Qiang Rong; Ke-Yin Ye; Shu-Li You
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-07       Impact factor: 15.336

5.  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

6.  Palladium-catalyzed enantioselective C-3 allylation of 3-substituted-1H-indoles using trialkylboranes.

Authors:  Barry M Trost; Jean Quancard
Journal:  J Am Chem Soc       Date:  2006-05-17       Impact factor: 15.419

7.  Remarkably reactive dihydroindoloindoles via palladium-catalysed dearomatisation.

Authors:  Robin B Bedford; Natalie Fey; Mairi F Haddow; Rosalind F Sankey
Journal:  Chem Commun (Camb)       Date:  2011-02-16       Impact factor: 6.222

8.  Palladium-catalyzed beta-allylation of 2,3-disubstituted indoles.

Authors:  Natsuko Kagawa; Jeremiah P Malerich; Viresh H Rawal
Journal:  Org Lett       Date:  2008-05-21       Impact factor: 6.005

9.  Palladium-catalyzed enantioselective alpha-arylation and alpha-vinylation of oxindoles facilitated by an axially chiral P-stereogenic ligand.

Authors:  Alexander M Taylor; Ryan A Altman; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-07-29       Impact factor: 15.419

10.  Oxidative Friedel-Crafts reaction and its application to the total syntheses of Amaryllidaceae alkaloids.

Authors:  Kimiaka C Guérard; Cyrille Sabot; Léanne Racicot; Sylvain Canesi
Journal:  J Org Chem       Date:  2009-03-06       Impact factor: 4.354
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  15 in total

1.  Intercepting Wacker intermediates with arenes: C-H functionalization and dearomatization.

Authors:  Bryan S Matsuura; Allison G Condie; Ian A McBee; Ryan C Buff; Gregory J Karahalis; Corey R J Stephenson
Journal:  Org Lett       Date:  2011-11-09       Impact factor: 6.005

2.  Recent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods.

Authors:  Hem Raj Khatri; Nolan Carney; Ryan Rutkoski; Bijay Bhattarai; Pavel Nagorny
Journal:  European J Org Chem       Date:  2020-01-01

3.  Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

Authors:  Louis-Charles Campeau; Nilay Hazari
Journal:  Organometallics       Date:  2018-11-27       Impact factor: 3.876

4.  DFT studies on the palladium-catalyzed dearomatization reaction between naphthalene allyl chloride and allyltributylstannane.

Authors:  Wei Cao; Dongxu Tian; Dongxue Han
Journal:  J Mol Model       Date:  2015-09-16       Impact factor: 1.810

5.  Synthesis of enantiomerically enriched imidazolidin-2-ones through asymmetric palladium-catalyzed alkene carboamination reactions.

Authors:  Brett A Hopkins; John P Wolfe
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-31       Impact factor: 15.336

6.  Investigating the dearomative rearrangement of biaryl phosphine-ligated Pd(II) complexes.

Authors:  Phillip J Milner; Thomas J Maimone; Mingjuan Su; Jiahao Chen; Peter Müller; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2012-11-27       Impact factor: 15.419

7.  Activation of allylic esters in an intramolecular vinylogous kinetic resolution reaction with synergistic magnesium catalysts.

Authors:  Dan Li; Yuling Yang; Minmin Zhang; Linqing Wang; Yingfan Xu; Dongxu Yang; Rui Wang
Journal:  Nat Commun       Date:  2020-05-22       Impact factor: 14.919

8.  A Simple and Broadly Applicable C-N Bond Forming Dearomatization Protocol Enabled by Bifunctional Amino Reagents.

Authors:  Xiaofeng Ma; Joshua J Farndon; Tom A Young; Natalie Fey; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-11       Impact factor: 15.336

9.  Organocatalytic asymmetric chlorinative dearomatization of naphthols.

Authors:  Qin Yin; Shou-Guo Wang; Xiao-Wei Liang; De-Wei Gao; Jun Zheng; Shu-Li You
Journal:  Chem Sci       Date:  2015-04-27       Impact factor: 9.825

10.  Efficient syntheses of (-)-crinine and (-)-aspidospermidine, and the formal synthesis of (-)-minfiensine by enantioselective intramolecular dearomative cyclization.

Authors:  Kang Du; He Yang; Pan Guo; Liang Feng; Guangqing Xu; Qinghai Zhou; Lung Wa Chung; Wenjun Tang
Journal:  Chem Sci       Date:  2017-07-03       Impact factor: 9.825
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