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Literature DB >> 21126097

Intermolecular [3 + 3]-cycloadditions of azides with the Nazarov intermediate.

Owen Scadeng¹, Michael J Ferguson, F G West.

Abstract

Tetrasubstituted 1,4-dien-3-ones undergo Nazarov cyclization at low temperature, followed by reaction with organic azides via an apparent [3 + 3]-cycloaddition to give bridged bicyclic triazenes. These products do not appear to be intermediates in the previously described Schmidt-type process to furnish dihydropyridones. The reaction typically occurs with high diastereoselectivity.

Entities: Chemical

Year: 2010 PMID： 21126097 DOI： 10.1021/ol102651k

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

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Cited

9 in total

1. Using Nazarov electrocyclization to stage chemoselective [1,2]-migrations: stereoselective synthesis of functionalized cyclopentenones.

Authors: David Lebœuf; Jie Huang; Vincent Gandon; Alison J Frontier
Journal: Angew Chem Int Ed Engl Date: 2011-09-26 Impact factor: 15.336

2. Total synthesis of (±)-rocaglamide via oxidation-initiated Nazarov cyclization.

Authors: John A Malona; Kevin Cariou; William T Spencer; Alison J Frontier
Journal: J Org Chem Date: 2012-01-26 Impact factor: 4.354

3. Efficient Nazarov cyclization/Wagner-Meerwein rearrangement terminated by a Cu(II)-promoted oxidation: synthesis of 4-alkylidene cyclopentenones.

Authors: David Lebœuf; Eric Theiste; Vincent Gandon; Stephanie L Daifuku; Michael L Neidig; Alison J Frontier
Journal: Chemistry Date: 2013-02-21 Impact factor: 5.236

4. Experimental and theoretical studies on the Nazarov cyclization/Wagner-Meerwein rearrangement sequence.

Authors: David Lebœuf; Vincent Gandon; Jennifer Ciesielski; Alison J Frontier
Journal: J Am Chem Soc Date: 2012-04-03 Impact factor: 15.419

5. Understanding the fate of the oxyallyl cation following Nazarov electrocyclization: sequential Wagner-Meerwein migrations and the synthesis of spirocyclic cyclopentenones.

Authors: Jie Huang; David Lebœuf; Alison J Frontier
Journal: J Am Chem Soc Date: 2011-04-05 Impact factor: 15.419

Intermolecular [3 + 3]-cycloadditions of azides with the Nazarov intermediate.

1. Using Nazarov electrocyclization to stage chemoselective [1,2]-migrations: stereoselective synthesis of functionalized cyclopentenones.

2. Total synthesis of (±)-rocaglamide via oxidation-initiated Nazarov cyclization.

3. Efficient Nazarov cyclization/Wagner-Meerwein rearrangement terminated by a Cu(II)-promoted oxidation: synthesis of 4-alkylidene cyclopentenones.

4. Experimental and theoretical studies on the Nazarov cyclization/Wagner-Meerwein rearrangement sequence.

5. Understanding the fate of the oxyallyl cation following Nazarov electrocyclization: sequential Wagner-Meerwein migrations and the synthesis of spirocyclic cyclopentenones.

6. Conjugate addition-initiated Nazarov cyclization.

7. α-Aryl-substituted allenamides in an imino-Nazarov cyclization cascade catalyzed by Au(I).

8. Direct access to poly(glycidyl azide) and its copolymers through anionic (co-)polymerization of glycidyl azide.

9. The first intermolecular interrupted imino-Nazarov reaction: expeditious access to carbocyclic nucleoside analogues.