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Literature DB >> 11554825

1,2-aryl and 1,2-hydride migration in transition metal complex catalyzed diazo decomposition: a novel approach to alpha-aryl-beta-enamino esters.

Abstract

N-Tosyl diazoketamines were prepared by addition of the ethyl alpha-diazoacetate anion to N-sulfonylimines. The diazo decomposition of the diazoketamines with Rh(2)(OAc)(4) complex resulted in aryl migration to give alpha-aryl-beta-enamino esters in good yields and high stereoselectivity. The effect of the catalysts on the migratory aptitude of 1,2-aryl over 1,2-hydride migration was studied. A reaction mechanism involving a "bridged" phenonium ion is proposed. Reaction: see text.

Entities: Chemical

Year: 2001 PMID： 11554825 DOI： 10.1021/ol016324p

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

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Cited

6 in total

1. A new reactivity mode for the diazo group: diastereoselective 1,3-aminoalkylation reaction of β-amino-α-diazoesters to give triazolines.

Authors: Alexey Kuznetsov; Anton V Gulevich; Donald J Wink; Vladimir Gevorgyan
Journal: Angew Chem Int Ed Engl Date: 2014-07-01 Impact factor: 15.336

2. Pyridine group assisted addition of diazo-compounds to imines in the 3-CC reaction of 2-aminopyridines, aldehydes, and diazo-compounds.

Authors: Anton V Gulevich; Victoria Helan; Donald J Wink; Vladimir Gevorgyan
Journal: Org Lett Date: 2013-02-01 Impact factor: 6.005

3. Elusive metal-free primary amination of arylboronic acids: synthetic studies and mechanism by density functional theory.

Authors: Chen Zhu; Gongqiang Li; Daniel H Ess; John R Falck; László Kürti
Journal: J Am Chem Soc Date: 2012-10-25 Impact factor: 15.419

1,2-aryl and 1,2-hydride migration in transition metal complex catalyzed diazo decomposition: a novel approach to alpha-aryl-beta-enamino esters.

1. A new reactivity mode for the diazo group: diastereoselective 1,3-aminoalkylation reaction of β-amino-α-diazoesters to give triazolines.

2. Pyridine group assisted addition of diazo-compounds to imines in the 3-CC reaction of 2-aminopyridines, aldehydes, and diazo-compounds.

3. Elusive metal-free primary amination of arylboronic acids: synthetic studies and mechanism by density functional theory.

4. Formation of synthetically relevant CF₃-substituted phenonium ions in superacid media.

5. A DFT calculation-inspired Rh(i)-catalyzed reaction via suppression of α-H shift in α-alkyldiazoacetates.

6. Copper-catalyzed direct transformation of simple alkynes to alkenyl nitriles via aerobic oxidative N-incorporation.

1,2-aryl and 1,2-hydride migration in transition metal complex catalyzed diazo decomposition: a novel approach to alpha-aryl-beta-enamino esters.

1. A new reactivity mode for the diazo group: diastereoselective 1,3-aminoalkylation reaction of β-amino-α-diazoesters to give triazolines.

2. Pyridine group assisted addition of diazo-compounds to imines in the 3-CC reaction of 2-aminopyridines, aldehydes, and diazo-compounds.

3. Elusive metal-free primary amination of arylboronic acids: synthetic studies and mechanism by density functional theory.

4. Formation of synthetically relevant CF3-substituted phenonium ions in superacid media.

5. A DFT calculation-inspired Rh(i)-catalyzed reaction via suppression of α-H shift in α-alkyldiazoacetates.

6. Copper-catalyzed direct transformation of simple alkynes to alkenyl nitriles via aerobic oxidative N-incorporation.

4. Formation of synthetically relevant CF₃-substituted phenonium ions in superacid media.