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Literature DB >> 25124085

Asymmetric gold-catalyzed lactonizations in water at room temperature.

Sachin Handa¹, Daniel J Lippincott, Donald H Aue, Bruce H Lipshutz.

Abstract

Asymmetric gold-catalyzed hydrocarboxylations are reported that show broad substrate scope. The hydrophobic effect associated with in situ-formed aqueous nanomicelles gives good to excellent ee's of product lactones. In-flask product isolation, along with the recycling of the catalyst and the reaction medium, are combined to arrive at an especially environmentally friendly process.

Entities: Chemical Disease Gene Species

Keywords: asymmetric catalysis; gold catalysis; micellar catalysis; surfactants

Mesh：

Substances：
Lactones
Water
Gold

Year: 2014 PMID： 25124085 PMCID： PMC4193796 DOI： 10.1002/anie.201404729

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

26 in total

1. Gold(I)-catalyzed dynamic kinetic enantioselective intramolecular hydroamination of allenes.

Authors: Zhibin Zhang; Christopher F Bender; Ross A Widenhoefer
Journal: J Am Chem Soc Date: 2007-10-30 Impact factor: 15.419

Review 2. Gold-catalyzed organic transformations.

Authors: Zigang Li; Chad Brouwer; Chuan He
Journal: Chem Rev Date: 2008-07-10 Impact factor: 60.622

3. A new type of chiral sulfinamide monophosphine ligands: stereodivergent synthesis and application in enantioselective gold(I)-catalyzed cycloaddition reactions.

Authors: Zhan-Ming Zhang; Peng Chen; Wenbo Li; Yanfei Niu; Xiao-Li Zhao; Junliang Zhang
Journal: Angew Chem Int Ed Engl Date: 2014-03-20 Impact factor: 15.336

4. Recent developments in enantioselective gold(I) catalysis.

Authors: Ross A Widenhoefer
Journal: Chemistry Date: 2008 Impact factor: 5.236

5. Mechanistic analysis of gold(I)-catalyzed intramolecular allene hydroalkoxylation reveals an off-cycle bis(gold) vinyl species and reversible C-O bond formation.

Authors: Timothy J Brown; Dieter Weber; Michel R Gagné; Ross A Widenhoefer
Journal: J Am Chem Soc Date: 2012-05-29 Impact factor: 15.419

6. Silver-catalysed enantioselective addition of O-H and N-H bonds to allenes: a new model for stereoselectivity based on noncovalent interactions.

Authors: Jannine L Arbour; Henry S Rzepa; Julia Contreras-García; Luis A Adrio; Elena M Barreiro; King Kuok Hii
Journal: Chemistry Date: 2012-07-24 Impact factor: 5.236

7. Helicenes with embedded phosphole units in enantioselective gold catalysis.

Authors: Keihann Yavari; Paul Aillard; Yang Zhang; Frédérick Nuter; Pascal Retailleau; Arnaud Voituriez; Angela Marinetti
Journal: Angew Chem Int Ed Engl Date: 2013-12-06 Impact factor: 15.336

8. Enantioselective alkynylbenzaldehyde cyclizations catalyzed by chiral gold(I) acyclic diaminocarbene complexes containing weak Au-arene interactions.

Authors: Sachin Handa; LeGrande M Slaughter
Journal: Angew Chem Int Ed Engl Date: 2012-01-04 Impact factor: 15.336

9. Gold(I)-catalyzed intramolecular enantioselective hydroarylation of allenes with indoles.

Authors: Cong Liu; Ross A Widenhoefer
Journal: Org Lett Date: 2007-04-12 Impact factor: 6.005

10. Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses.

Authors: Yin-Wei Sun; Qin Xu; Min Shi
Journal: Beilstein J Org Chem Date: 2013-10-28 Impact factor: 2.883

8 in total

1. HandaPhos: A General Ligand Enabling Sustainable ppm Levels of Palladium-Catalyzed Cross-Couplings in Water at Room Temperature.

Authors: Sachin Handa; Martin P Andersson; Fabrice Gallou; John Reilly; Bruce H Lipshutz
Journal: Angew Chem Int Ed Engl Date: 2016-02-29 Impact factor: 15.336

Asymmetric gold-catalyzed lactonizations in water at room temperature.

1. Gold(I)-catalyzed dynamic kinetic enantioselective intramolecular hydroamination of allenes.

Review 2. Gold-catalyzed organic transformations.

3. A new type of chiral sulfinamide monophosphine ligands: stereodivergent synthesis and application in enantioselective gold(I)-catalyzed cycloaddition reactions.

4. Recent developments in enantioselective gold(I) catalysis.

5. Mechanistic analysis of gold(I)-catalyzed intramolecular allene hydroalkoxylation reveals an off-cycle bis(gold) vinyl species and reversible C-O bond formation.

6. Silver-catalysed enantioselective addition of O-H and N-H bonds to allenes: a new model for stereoselectivity based on noncovalent interactions.

7. Helicenes with embedded phosphole units in enantioselective gold catalysis.

8. Enantioselective alkynylbenzaldehyde cyclizations catalyzed by chiral gold(I) acyclic diaminocarbene complexes containing weak Au-arene interactions.

9. Gold(I)-catalyzed intramolecular enantioselective hydroarylation of allenes with indoles.

10. Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses.

1. HandaPhos: A General Ligand Enabling Sustainable ppm Levels of Palladium-Catalyzed Cross-Couplings in Water at Room Temperature.

2. Nanonickel-catalyzed Suzuki-Miyaura cross-couplings in water.

3. Interplay of Polarity and Confinement in Asymmetric Catalysis with Chiral Rh Diene Complexes in Microemulsions.

Review 4. Catalytic Asymmetric Hydroalkoxylation of C-C Multiple Bonds.

5. H-Bonded Counterion-Directed Enantioselective Au(I) Catalysis.

6. Micellar catalysis-enabled sustainable ppm Au-catalyzed reactions in water at room temperature.

7. Gold-catalyzed stereoselective cycloisomerization of allenoic acids for two types of common natural γ-butyrolactones.

8. Construction of spirocarbocycles via gold-catalyzed intramolecular dearomatization of naphthols.