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Literature DB >> 29498865

Regiocontrolled Wacker Oxidation of Cinnamyl Azides.

Angela S Carlson¹, Cristian Calcanas¹, Ryan M Brunner¹, Joseph J Topczewski¹.

Abstract

A highly regioselective Wacker oxidation has been developed for the oxidation of cinnamyl azides. The catalytic oxidation tolerates the azide functionality, and more than 15 β-azido ketones were isolated (25-92% yield). High regioselectivity for the aryl ketone is observed in all cases. A robustness screen was conducted to determine functional group tolerance. The products of the oxidaiton can be readily diversified.

Entities: Chemical Gene

Mesh：

Substances：
Azides
Ketones

Year: 2018 PMID： 29498865 PMCID： PMC5989718 DOI： 10.1021/acs.orglett.8b00344

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

23 in total

1. Regioselective Wacker oxidation of internal alkenes: rapid access to functionalized ketones facilitated by cross-metathesis.

Authors: Bill Morandi; Zachary K Wickens; Robert H Grubbs
Journal: Angew Chem Int Ed Engl Date: 2013-07-26 Impact factor: 15.336

2. Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of Tetralins, Chromanes, and Tetrahydroquinolines.

Authors: Matthew R Porter; Rami M Shaker; Cristian Calcanas; Joseph J Topczewski
Journal: J Am Chem Soc Date: 2018-01-10 Impact factor: 15.419

3. Practical and general palladium-catalyzed synthesis of ketones from internal olefins.

Authors: Bill Morandi; Zachary K Wickens; Robert H Grubbs
Journal: Angew Chem Int Ed Engl Date: 2013-01-16 Impact factor: 15.336

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

Authors: Ken S Feldman; Joshua F Antoline
Journal: Org Lett Date: 2012-01-13 Impact factor: 6.005

5. Wacker-Type Oxidation Using an Iron Catalyst and Ambient Air: Application to Late-Stage Oxidation of Complex Molecules.

Authors: Binbin Liu; Fengli Jin; Tianjiao Wang; Xiaorong Yuan; Wei Han
Journal: Angew Chem Int Ed Engl Date: 2017-09-05 Impact factor: 15.336

6. Efficient total synthesis of (+)-dihydropinidine, (-)-epidihydropinidine, and (-)-pinidinone.

Authors: Miroslav Kavala; František Mathia; Jozef Kožíšek; Peter Szolcsányi
Journal: J Nat Prod Date: 2011-03-16 Impact factor: 4.050

7. Organic azides: an exploding diversity of a unique class of compounds.

Authors: Stefan Bräse; Carmen Gil; Kerstin Knepper; Viktor Zimmermann
Journal: Angew Chem Int Ed Engl Date: 2005-08-19 Impact factor: 15.336

8. Hypervalent Iodine as a Terminal Oxidant in Wacker-Type Oxidation of Terminal Olefins to Methyl Ketones.

Authors: Dipali A Chaudhari; Rodney A Fernandes
Journal: J Org Chem Date: 2016-02-18 Impact factor: 4.354

9. Orbital-Overlap control in the solid-state reactivity of beta-azido-propiophenones: selective formation of cis-azo-dimers.

Authors: Jagadis Sankaranarayanan; Lauren N Bort; Sarah M Mandel; Ping Chen; Jeanette A Krause; Elwood E Brooks; Pearl Tsang; Anna D Gudmundsdottir
Journal: Org Lett Date: 2008-02-07 Impact factor: 6.005

10. Efficient conversion of primary azides to aldehydes catalyzed by active site variants of myoglobin.

Authors: Simone Giovani; Ritesh Singh; Rudi Fasan
Journal: Chem Sci Date: 2015-09-28 Impact factor: 9.825

6 in total

Review 1. Allylic azides: synthesis, reactivity, and the Winstein rearrangement.

Authors: Angela S Carlson; Joseph J Topczewski
Journal: Org Biomol Chem Date: 2019-05-08 Impact factor: 3.876

2. Dative Directing Group Effects in Ti-Catalyzed [2+2+1] Pyrrole Synthesis: Chemo- and Regioselective Alkyne Heterocoupling.

Authors: Hsin-Chun Chiu; Xin Yi See; Ian A Tonks
Journal: ACS Catal Date: 2018-11-29 Impact factor: 13.084