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Literature DB >> 29034684

Ynol Ethers as Ketene Equivalents in Rhodium-Catalyzed Intermolecular [5 + 2] Cycloaddition Reactions.

Paul A Wender¹, Christian Ebner¹, Brandon D Fennell¹, Fuyuhiko Inagaki¹, Birte Schröder¹.

Abstract

The previously unexplored metal-catalyzed [5 + 2] cycloadditions of vinylcyclopropanes (VCPs) and electron-rich alkynes (ynol ethers) have been found to provide a highly efficient, direct route to dioxygenated seven-membered rings, a common feature of numerous natural and non-natural targets and building blocks for synthesis. The reactions proceed in high yield at room temperature and tolerate a broad range of functionalities. Substituted VCPs were found to react with high regioselectivity.

Entities: Chemical Species

Mesh：

Substances：

Year: 2017 PMID： 29034684 PMCID： PMC5833981 DOI： 10.1021/acs.orglett.7b02765

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

39 in total

1. Iridium-Catalyzed [5 + 1] Cycloaddition: Allenylcyclopropane as a Five-Carbon Assembling Unit.

Authors: Masahiro Murakami; Kenichiro Itami; Minoru Ubukata; Itaru Tsuji; Yoshihiko Ito
Journal: J Org Chem Date: 1998-01-09 Impact factor: 4.354

2. The first century of ketenes (1905-2005): the birth of a versatile family of reactive intermediates.

Authors: Thomas T Tidwell
Journal: Angew Chem Int Ed Engl Date: 2005-09-12 Impact factor: 15.336

3. Palladium-catalyzed synthesis of substituted cycloheptane-1,4-diones by an asymmetric ring-expanding allylation (AREA).

Authors: Sabrina R Schulz; Siegfried Blechert
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

4. First total synthesis of antiostatin A1, a potent carbazole-based naturally occurring antioxidant.

Authors: Carole Alayrac; Dieter Schollmeyer; Bernhard Witulski
Journal: Chem Commun (Camb) Date: 2009-02-18 Impact factor: 6.222

5. Selectivity in nickel-catalyzed rearrangements of cyclopropylen-ynes.

Authors: Gang Zuo; Janis Louie
Journal: J Am Chem Soc Date: 2005-04-27 Impact factor: 15.419

6. Catalytic Efficiency Is a Function of How Rhodium(I) (5 + 2) Catalysts Accommodate a Conserved Substrate Transition State Geometry: Induced Fit Model for Explaining Transition Metal Catalysis.

Authors: Thomas J L Mustard; Paul A Wender; Paul Ha-Yeon Cheong
Journal: ACS Catal Date: 2015-03-06 Impact factor: 13.084

7. A cheap metal for a "noble" task: preparative and mechanistic aspects of cycloisomerization and cycloaddition reactions catalyzed by low-valent iron complexes.

Authors: Alois Fürstner; Keisuke Majima; Rubén Martín; Helga Krause; Egmont Kattnig; Richard Goddard; Christian W Lehmann
Journal: J Am Chem Soc Date: 2008-01-16 Impact factor: 15.419

Ynol Ethers as Ketene Equivalents in Rhodium-Catalyzed Intermolecular [5 + 2] Cycloaddition Reactions.

1. Iridium-Catalyzed [5 + 1] Cycloaddition: Allenylcyclopropane as a Five-Carbon Assembling Unit.

2. The first century of ketenes (1905-2005): the birth of a versatile family of reactive intermediates.

3. Palladium-catalyzed synthesis of substituted cycloheptane-1,4-diones by an asymmetric ring-expanding allylation (AREA).

4. First total synthesis of antiostatin A1, a potent carbazole-based naturally occurring antioxidant.

5. Selectivity in nickel-catalyzed rearrangements of cyclopropylen-ynes.

6. Catalytic Efficiency Is a Function of How Rhodium(I) (5 + 2) Catalysts Accommodate a Conserved Substrate Transition State Geometry: Induced Fit Model for Explaining Transition Metal Catalysis.

7. A cheap metal for a "noble" task: preparative and mechanistic aspects of cycloisomerization and cycloaddition reactions catalyzed by low-valent iron complexes.

8. Rhodium-Catalyzed Stereoselective Intramolecular [5 + 2] Cycloaddition of 3-Acyloxy 1,4-Enyne and Alkene.

9. Computational ligand design in enantio- and diastereoselective ynamide [5+2] cycloisomerization.

10. Rhodium-catalyzed linear codimerization and cycloaddition of ketenes with alkynes.

1. Transition Metal-Catalyzed Selective Carbon-Carbon Bond Cleavage of Vinylcyclopropanes in Cycloaddition Reactions.