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Literature DB >> 19388652

Palladium-catalyzed asymmetric dearomatization of naphthalene derivatives.

Jorge García-Fortanet¹, Florian Kessler, Stephen L Buchwald.

Abstract

An intramolecular enantioselective metal-catalyzed dearomatization reaction is described. This procedure allows the dearomatization of naphthalene derivatives through an electrophilic aromatic substitution-type reaction on a Pd(II) intermediate. The high yields and enantioselectivities achieved make this procedure a valuable method for synthetic chemists.

Entities: Chemical Gene

Mesh：

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Year: 2009 PMID： 19388652 PMCID： PMC2748791 DOI： 10.1021/ja9025193

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

8 in total

1. Enantioselective construction of quaternary stereocenter through a Reissert-type reaction catalyzed by an electronically tuned bifunctional catalyst: efficient synthesis of various biologically significant compounds.

Authors: K Funabashi; H Ratni; M Kanai; M Shibasaki
Journal: J Am Chem Soc Date: 2001-10-31 Impact factor: 15.419

2. Transition-metal-mediated dearomatization reactions.

Authors: A R Pape; K P Kaliappan; E P Kündig
Journal: Chem Rev Date: 2000-08-09 Impact factor: 60.622

3. Catalytic asymmetric vinylation of ketone enolates.

Authors: A Chieffi; K Kamikawa; J Ahman; J M Fox; S L Buchwald
Journal: Org Lett Date: 2001-06-14 Impact factor: 6.005

4. An enantioselective organocatalytic oxidative dearomatization strategy.

Authors: Ngoc T Vo; Robert D M Pace; Fionn O'Hara; Matthew J Gaunt
Journal: J Am Chem Soc Date: 2008-01-16 Impact factor: 15.419

5. 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

6. New modes of reactivity in the threshold of the reduction potential in solution. Alkylation of lithium PAH (polycyclic aromatic hydrocarbon) dianions by primary fluoroalkanes: a reaction pathway complementing the classical birch reductive alkylation.

Authors: Cristóbal Melero; Raquel P Herrera; Albert Guijarro; Miguel Yus
Journal: Chemistry Date: 2007 Impact factor: 5.236

7. Catalytic asymmetric synthesis of all-carbon quaternary stereocenters.

Authors: Christopher J Douglas; Larry E Overman
Journal: Proc Natl Acad Sci U S A Date: 2004-01-14 Impact factor: 11.205

Review 8. Contiguous stereogenic quaternary carbons: a daunting challenge in natural products synthesis.

Authors: Emily A Peterson; Larry E Overman
Journal: Proc Natl Acad Sci U S A Date: 2004-07-01 Impact factor: 11.205

8 in total

17 in total

1. Palladium-Catalyzed Dearomative syn-1,4-Carboamination.

Authors: Mikiko Okumura; Alexander S Shved; David Sarlah
Journal: J Am Chem Soc Date: 2017-12-05 Impact factor: 15.419

2. Palladium-Catalyzed Dearomative syn-1,4-Diamination.

Authors: William C Wertjes; Mikiko Okumura; David Sarlah
Journal: J Am Chem Soc Date: 2018-12-21 Impact factor: 15.419

3. 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

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. Catalytic enantioselective alkylative dearomatization-annulation: total synthesis and absolute configuration assignment of hyperibone K.

Authors: Ji Qi; Aaron B Beeler; Qiang Zhang; John A Porco
Journal: J Am Chem Soc Date: 2010-10-06 Impact factor: 15.419