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Literature DB >> 16316224

Tandem au-catalyzed 3,3-rearrangement-[2 + 2] cycloadditions of propargylic esters: expeditious access to highly functionalized 2,3-indoline-fused cyclobutanes.

Abstract

The treatment of readily available propargylic indole-3-acetates with a catalytic amount of AuCl(PPh3)/AgSbF6 leads to tandem activations of the propargylic esters and the in situ generated allenylic esters, resulting in expeditious access to highly functionalized cyclobutanes with fused 2,3-indoline and gamma-lactone rings and an exocyclic E-double bond through sequential 3,3-rearrangement and [2 + 2] cyclization.

Entities: Chemical Gene

Year: 2005 PMID： 16316224 DOI： 10.1021/ja056419c

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

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Cited

46 in total

1. The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: an efficient synthesis of (1Z, 3E)-1-bromo/chloro-2-carboxy-1,3-dienes.

Authors: Yanzhao Wang; Biao Lu; Liming Zhang
Journal: Chem Commun (Camb) Date: 2010-10-29 Impact factor: 6.222

2. Gold-catalyzed 1,2-migration of silicon, tin, and germanium en route to C-2 substituted fused pyrrole-containing heterocycles.

Authors: Ilya V Seregin; Vladimir Gevorgyan
Journal: J Am Chem Soc Date: 2006-09-20 Impact factor: 15.419

Tandem au-catalyzed 3,3-rearrangement-[2 + 2] cycloadditions of propargylic esters: expeditious access to highly functionalized 2,3-indoline-fused cyclobutanes.

1. The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: an efficient synthesis of (1Z, 3E)-1-bromo/chloro-2-carboxy-1,3-dienes.

2. Gold-catalyzed 1,2-migration of silicon, tin, and germanium en route to C-2 substituted fused pyrrole-containing heterocycles.

3. Gold-catalyzed cycloisomerization of 1,5-allenynes via dual activation of an ene reaction.

4. Heterocycles via intramolecular platinum-catalyzed propargylic substitution.

5. Gold-catalyzed Intermolecular [4C + 3C] Cycloaddition Reactions.

6. Rhodium-catalyzed ring expansion of cyclopropanes to seven-membered rings by 1,5 C-C bond migration.

7. Multisubstituted N-fused heterocycles via transition metal-catalyzed cycloisomerization protocols.

Review 8. Metal-catalyzed double migratory cascade reactions of propargylic esters and phosphates.

9. Gold-catalyzed transannular [4+3] cycloaddition reactions.

10. Mechanistic studies on Au(I)-catalyzed [3,3]-sigmatropic rearrangements using cyclopropane probes.