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Literature DB >> 18345683

Allenyl azide cycloaddition chemistry. photochemical initiation and CuI mediation leads to improved regioselectivity.

Ken S Feldman¹, D Keith Hester, Carlos Silva López, Olalla Nieto Faza.

Abstract

Irradiation of 2-(3-alkenyl)allenylphenyl azides in the presence of excess CuI furnished functionalized 2,3-cyclopentenylindoles in good yield with only trace amounts of competitive C-N-bonded regioisomeric products. These results represent a significant departure from the modest-to-nonexistent regioselectivity that attended thermal cyclization of these allenyl azide substrates.

Entities: Chemical

Mesh：

Substances：

Year: 2008 PMID： 18345683 PMCID： PMC2788436 DOI： 10.1021/ol800429j

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

4 in total

1. Rapid injection NMR in mechanistic organocopper chemistry. Preparation of the elusive copper(III) intermediate.

Authors: Steven H Bertz; Stephen Cope; Michael Murphy; Craig A Ogle; Brad J Taylor
Journal: J Am Chem Soc Date: 2007-05-17 Impact factor: 15.419

2. Allenyl azide cycloaddition chemistry. Synthesis of annelated indoles from 2-(allenyl)phenyl azide substrates.

Authors: Ken S Feldman; Malliga R Iyer; D Keith Hester
Journal: Org Lett Date: 2006-07-06 Impact factor: 6.005

3. Construction of azacycles based on endo-mode cyclization of allenes.

Authors: Chisato Mukai; Minoru Kobayashi; Shoko Kubota; Yukie Takahashi; Shinji Kitagaki
Journal: J Org Chem Date: 2004-03-19 Impact factor: 4.354

4. Cyclization cascade of allenyl azides: a dual mechanism.

Authors: Carlos Silva López; Olalla Nieto Faza; Ken S Feldman; Malliga R Iyer; D Keith Hester Ii
Journal: J Am Chem Soc Date: 2007-05-27 Impact factor: 15.419

4 in total

5 in total

Allenyl azide cycloaddition chemistry. photochemical initiation and CuI mediation leads to improved regioselectivity.

1. Rapid injection NMR in mechanistic organocopper chemistry. Preparation of the elusive copper(III) intermediate.

2. Allenyl azide cycloaddition chemistry. Synthesis of annelated indoles from 2-(allenyl)phenyl azide substrates.

3. Construction of azacycles based on endo-mode cyclization of allenes.

4. Cyclization cascade of allenyl azides: a dual mechanism.

1. Allenyl azide cycloaddition chemistry. 2,3-cyclopentennelated indole synthesis through indolidene intermediates.

2. Allenyl azide cycloaddition chemistry: application to the total synthesis of (±)-meloscine.

3. Cyclization Cascade of Allenyl Azides: Synergy Between Theory and Experiment.

4. Synthesis studies on the Melodinus alkaloid meloscine.

5. Nazarov cyclization of 1,4-pentadien-3-ols: preparation of cyclopenta[b]indoles and spiro[indene-1,4'-quinoline]s.