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Literature DB >> 21916520

Synthesis of fused carbocycles via a selective 6-endo dig gold(I)-catalyzed carbocyclization.

Francis Barabé¹, Patrick Levesque, Ilia Korobkov, Louis Barriault.

Abstract

A gold-catalyzed synthesis of fused carbocycles via a regioselective 6-endo dig process is reported. The selectivity can be modulated by the steric and electronic properties of gold(I) complexes. The ligands can influence the pathway selectivity for the first bond formation rather than through a common intermediate generated after an initial bond formation. This gold(I)-catalyzed transformation provides access to synthetically useful carbocyclic motifs that are found in numerous diterpenoid natural products.

Entities: Chemical

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Year: 2011 PMID： 21916520 DOI： 10.1021/ol202314q

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

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Cited

12 in total

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Authors: Satoshi Ueda; Siraj Ali; Brett P Fors; Stephen L Buchwald
Journal: J Org Chem Date: 2012-02-15 Impact factor: 4.354

2. Mechanisms for the synthesis of conjugated enynes from diphenylacetylene and trimethylsilylacetylene catalyzed by a nickel(0) complex: DFT study of ligand-controlled selectivity.

Authors: Cheng Huang; Rongxing He; Wei Shen; Ming Li
Journal: J Mol Model Date: 2015-05-03 Impact factor: 1.810

3. Gold(I)-Mediated Cycloisomerization/Cycloaddition Enables Bioinspired Syntheses of Neonectrolides B-E and Analogues.

Authors: Thomas J Purgett; Matthew W Dyer; Bryce Bickel; James McNeely; John A Porco
Journal: J Am Chem Soc Date: 2019-09-12 Impact factor: 15.419

4. Gold-catalyzed diastereoselective cycloisomerization of alkylidene-cyclopropane-bearing 1,6-diynes.

Authors: Hongchao Zheng; Laura L Adduci; Ryan J Felix; Michel R Gagné
Journal: Angew Chem Int Ed Engl Date: 2014-06-11 Impact factor: 15.336

5. Rapid access to chroman-3-ones through gold-catalyzed oxidation of propargyl aryl ethers.

Authors: Yanzhao Wang; Kegong Ji; Sylvester Lan; Liming Zhang
Journal: Angew Chem Int Ed Engl Date: 2012-01-13 Impact factor: 15.336

6. Gold(III)- versus gold(I)-induced cyclization: synthesis of six-membered mesoionic carbene and acyclic (aryl)(heteroaryl) carbene complexes.

Authors: Gaël Ung; Michele Soleilhavoup; Guy Bertrand
Journal: Angew Chem Int Ed Engl Date: 2012-11-21 Impact factor: 15.336

Synthesis of fused carbocycles via a selective 6-endo dig gold(I)-catalyzed carbocyclization.

1. Me3(OMe)tBuXPhos: a surrogate ligand for Me4tBuXPhos in palladium-catalyzed C-N and C-O bond-forming reactions.

2. Mechanisms for the synthesis of conjugated enynes from diphenylacetylene and trimethylsilylacetylene catalyzed by a nickel(0) complex: DFT study of ligand-controlled selectivity.

3. Gold(I)-Mediated Cycloisomerization/Cycloaddition Enables Bioinspired Syntheses of Neonectrolides B-E and Analogues.

4. Gold-catalyzed diastereoselective cycloisomerization of alkylidene-cyclopropane-bearing 1,6-diynes.

5. Rapid access to chroman-3-ones through gold-catalyzed oxidation of propargyl aryl ethers.

6. Gold(III)- versus gold(I)-induced cyclization: synthesis of six-membered mesoionic carbene and acyclic (aryl)(heteroaryl) carbene complexes.

7. Enantioselective cyclizations of silyloxyenynes catalyzed by cationic metal phosphine complexes.

8. A Catalytic Intermolecular Formal Ene Reaction between Ketone-Derived Silyl Enol Ethers and Alkynes.

9. Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

10. Gold-catalyzed enantioselective ring-expanding cycloisomerization of cyclopropylidene bearing 1,5-enynes.