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Literature DB >> 17378561

Nucleophilic acylation of o-quinone methides: an umpolung strategy for the synthesis of alpha-aryl ketones and benzofurans.

Anita E Mattson¹, Karl A Scheidt.

Abstract

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 17378561 PMCID： PMC2586065 DOI： 10.1021/ja068189n

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

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10 in total

1. Quinone Methide Alkylation of Deoxycytidine.

Authors: Steven E. Rokita; Jianhong Yang; Praveen Pande; William A. Greenberg
Journal: J Org Chem Date: 1997-05-02 Impact factor: 4.354

2. Conversion of alpha,beta-unsaturated aldehydes into saturated esters: an Umpolung reaction catalyzed by nucleophilic carbenes.

Authors: Audrey Chan; Karl A Scheidt
Journal: Org Lett Date: 2005-03-03 Impact factor: 6.005

3. An improved catalyst for the asymmetric arylation of ketone enolates.

Authors: Takayuki Hamada; André Chieffi; Jens Ahman; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2002-02-20 Impact factor: 15.419

4. Direct nucleophilic acylation of nitroalkenes promoted by a fluoride anion/thiourea combination.

Authors: Anita E Mattson; Andrea M Zuhl; Troy E Reynolds; Karl A Scheidt
Journal: J Am Chem Soc Date: 2006-04-19 Impact factor: 15.419

5. Catalytic additions of acylsilanes to imines: an acyl anion strategy for the direct synthesis of alpha-amino ketones.

Authors: Anita E Mattson; Karl A Scheidt
Journal: Org Lett Date: 2004-11-11 Impact factor: 6.005

6. Aromatase inhibitors from Broussonetia papyrifera.

Authors: D Lee; K P Bhat; H H Fong; N R Farnsworth; J M Pezzuto; A D Kinghorn
Journal: J Nat Prod Date: 2001-10 Impact factor: 4.050

7. Stereoselective total synthesis of (+/-)-thielocin A1beta.

Authors: Y Génisson; P C Tyler; R G Ball; R N Young
Journal: J Am Chem Soc Date: 2001-11-21 Impact factor: 15.419

8. Catalytic conjugate additions of carbonyl anions under neutral aqueous conditions.

Authors: Michael C Myers; Ashwin R Bharadwaj; Benjamin C Milgram; Karl A Scheidt
Journal: J Am Chem Soc Date: 2005-10-26 Impact factor: 15.419

9. Palladium-catalyzed alpha-arylation of carbonyl compounds and nitriles.

Authors: Darcy A Culkin; John F Hartwig
Journal: Acc Chem Res Date: 2003-04 Impact factor: 22.384

10. The thiazolium-catalyzed Sila-Stetter reaction: conjugate addition of acylsilanes to unsaturated esters and ketones.

Authors: Anita E Mattson; Ashwin R Bharadwaj; Karl A Scheidt
Journal: J Am Chem Soc Date: 2004-03-03 Impact factor: 15.419

10 in total

12 in total

1. Michael Additions of Highly Basic Enolates to ortho-Quinone Methides.

Authors: Robert S Lewis; Christopher J Garza; Ann T Dang; Te Kie A Pedro; William J Chain
Journal: Org Lett Date: 2015-04-23 Impact factor: 6.005

2. N-heterocyclic-carbene-catalyzed synthesis of 2-aryl indoles.

Authors: M Todd Hovey; Christopher T Check; Alexandra F Sipher; Karl A Scheidt
Journal: Angew Chem Int Ed Engl Date: 2014-07-14 Impact factor: 15.336

3. N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

Authors: Anna Lee; Karl A Scheidt
Journal: Chem Commun (Camb) Date: 2015-02-25 Impact factor: 6.222

Nucleophilic acylation of o-quinone methides: an umpolung strategy for the synthesis of alpha-aryl ketones and benzofurans.

1. Quinone Methide Alkylation of Deoxycytidine.

2. Conversion of alpha,beta-unsaturated aldehydes into saturated esters: an Umpolung reaction catalyzed by nucleophilic carbenes.

3. An improved catalyst for the asymmetric arylation of ketone enolates.

4. Direct nucleophilic acylation of nitroalkenes promoted by a fluoride anion/thiourea combination.

5. Catalytic additions of acylsilanes to imines: an acyl anion strategy for the direct synthesis of alpha-amino ketones.

6. Aromatase inhibitors from Broussonetia papyrifera.

7. Stereoselective total synthesis of (+/-)-thielocin A1beta.

8. Catalytic conjugate additions of carbonyl anions under neutral aqueous conditions.

9. Palladium-catalyzed alpha-arylation of carbonyl compounds and nitriles.

10. The thiazolium-catalyzed Sila-Stetter reaction: conjugate addition of acylsilanes to unsaturated esters and ketones.

1. Michael Additions of Highly Basic Enolates to ortho-Quinone Methides.

2. N-heterocyclic-carbene-catalyzed synthesis of 2-aryl indoles.

3. N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

4. N-Heterocyclic Carbene-Promoted Rauhut]Currier Reactions between Vinyl Sulfones and α,β-Unsaturated Aldehydes.

5. A formal [4 + 4] complementary ambiphile pairing reaction: a new cyclization pathway for ortho-quinone methides.

6. Development of an alkaloid-pyrone annulation: synthesis of pleiomaltinine.

7. Intermolecular Cross-Acyloin Reactions by Fluoride-Promoted Additions of O-Silyl Thiazolium Carbinols.

8. A dual Lewis base activation strategy for enantioselective carbene-catalyzed annulations.

9. Concise synthesis of pauciflorol F using a Larock annulation.

10. Copper-Catalyzed Borylative Aromatization of p-Quinone Methides: Enantioselective Synthesis of Dibenzylic Boronates.