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Literature DB >> 18720989

Interrupting the Nazarov cyclization with indoles.

Abstract

A carbon-terminated interrupted Nazarov reaction is described. The trimethylsilyl enol ethers derived from propargyl vinyl ketones undergo selective proton transfer at the distal acetylenic carbon atom to provide allenyl vinyl ketones as transient intermediates. In the presence of indoles, a cascade of reactions is initiated that converts the initially formed pentadienyl cations to cyclopentenones bearing a quaternary alpha carbon atom.

Entities: Chemical Species

Mesh：

Substances：
Indoles
Protons

Year: 2008 PMID： 18720989 PMCID： PMC2663042 DOI： 10.1021/ol801587u

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

22 in total

1. "Designer acids": combined acid catalysis for asymmetric synthesis.

Authors: Hisashi Yamamoto; Kentaro Futatsugi
Journal: Angew Chem Int Ed Engl Date: 2005-03-18 Impact factor: 15.336

2. Tandem Nazarov cyclization-michael addition sequence catalyzed by an Ir(III) complex.

Authors: Mesfin Janka; Wei He; Inga E Haedicke; Frank R Fronczek; Alison J Frontier; Richard Eisenberg
Journal: J Am Chem Soc Date: 2006-04-26 Impact factor: 15.419

3. Intramolecular azide trapping of the Nazarov intermediate: formation of peroxy-bridged indolizidinones via a deep-seated rearrangement and aerobic oxidation.

Authors: Ali Rostami; Yong Wang; Atta M Arif; Robert McDonald; F G West
Journal: Org Lett Date: 2007-01-26 Impact factor: 6.005

4. Highly efficient trapping of the Nazarov intermediate with substituted arenes.

Authors: C C Browder; F P Marmsäter; F G West
Journal: Org Lett Date: 2001-09-20 Impact factor: 6.005

5. A new approach to the nazarov reaction via sequential electrocyclic ring opening and ring closure.

Authors: Tina N Grant; F G West
Journal: J Am Chem Soc Date: 2006-07-26 Impact factor: 15.419

6. Domino electrocyclization/azide-capture/schmidt rearrangement of dienones: one-step synthesis of dihydropyridones from simple building blocks.

Authors: Dong Song; Ali Rostami; F G West
Journal: J Am Chem Soc Date: 2007-09-08 Impact factor: 15.419

7. Formal intermolecular 4 + 4 approach to cyclooctanoids: 4 + 3 capture of the Nazarov oxyallyl intermediate with simple 1,3-dienes.

Authors: Yong Wang; Brenden D Schill; Atta M Arif; F G West
Journal: Org Lett Date: 2003-07-24 Impact factor: 6.005

Interrupting the Nazarov cyclization with indoles.

1. "Designer acids": combined acid catalysis for asymmetric synthesis.

2. Tandem Nazarov cyclization-michael addition sequence catalyzed by an Ir(III) complex.

3. Intramolecular azide trapping of the Nazarov intermediate: formation of peroxy-bridged indolizidinones via a deep-seated rearrangement and aerobic oxidation.

4. Highly efficient trapping of the Nazarov intermediate with substituted arenes.

5. A new approach to the nazarov reaction via sequential electrocyclic ring opening and ring closure.

6. Domino electrocyclization/azide-capture/schmidt rearrangement of dienones: one-step synthesis of dihydropyridones from simple building blocks.

7. Formal intermolecular 4 + 4 approach to cyclooctanoids: 4 + 3 capture of the Nazarov oxyallyl intermediate with simple 1,3-dienes.

8. Construction of aryl-substituted triquinanes through the interrupted Nazarov reaction.

9. Cationic cyclopentannelation of allene ethers.

10. Total synthesis of (+/-)-terpestacin and (+/-)-11-epi-terpestacin.

1. Beyond the Divinyl Ketone: Innovations in the Generation and Nazarov Cyclization of Pentadienyl Cation Intermediates.

2. Enamine-iminium ion Nazarov cyclization of alpha-ketoenones.