Literature DB >> 21207600

Recent developments in methodology for the direct oxyamination of olefins.

Timothy J Donohoe1, Cedric K A Callens, Aida Flores, Adam R Lacy, Akshat H Rathi.   

Abstract

1,2-Amino alcohols are high-value, versatile functional groups that are found in scores of biologically active molecules and other interesting synthetic targets such as ligands and auxiliaries. Given their prominent position within organic compounds of import, it is no surprise to note that many routes have been developed to access this motif and there are many different starting points from which a synthetic chemist might embark on a synthesis. However, one particular approach stands out from the others, and this is the direct conversion of an alkene to a vicinal amino alcohol derivative (oxyamination). Research in this field has been particularly active in recent years and many interesting new methodologies have been reported. The purpose of this review is to give the reader a tour of the methods that have emerged in the last few years so one can appreciate the myriad of different metals and reagents that can accomplish the oxyamination of alkenes. There are still many challenges to be overcome and, herein, we also outline the areas that are ripe for further development and which bode well for the future.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2010        PMID: 21207600     DOI: 10.1002/chem.201002323

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  31 in total

1.  Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis.

Authors:  Nicholas L Reed; Madeline I Herman; Vladimir P Miltchev; Tehshik P Yoon
Journal:  Org Lett       Date:  2018-11-08       Impact factor: 6.005

2.  Copper-Catalyzed 1,2-Amino Oxygenation of 1,3-Dienes: A Chemo-, Regio-, and Site-Selective Three-Component Reaction with O-Acylhydroxylamines and Carboxylic Acids.

Authors:  Brett N Hemric; Andy W Chen; Qiu Wang
Journal:  ACS Catal       Date:  2019-09-24       Impact factor: 13.084

3.  Copper-Catalyzed Modular Amino Oxygenation of Alkenes: Access to Diverse 1,2-Amino Oxygen-Containing Skeletons.

Authors:  Brett N Hemric; Andy W Chen; Qiu Wang
Journal:  J Org Chem       Date:  2019-01-17       Impact factor: 4.354

Review 4.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

5.  Stereoselective synthesis of morpholines via copper-promoted oxyamination of alkenes.

Authors:  Fatima C Sequeira; Sherry R Chemler
Journal:  Org Lett       Date:  2012-08-15       Impact factor: 6.005

6.  Intramolecular aminocyanation of alkenes by N-CN bond cleavage.

Authors:  Zhongda Pan; Sarah M Pound; Naveen R Rondla; Christopher J Douglas
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-09       Impact factor: 15.336

7.  Stereoselective Copper-Catalyzed Intramolecular Alkene Aminooxygenation: Effects of Substrate and Ligand Structure on Selectivity.

Authors:  Monissa C Paderes; Sherry R Chemler
Journal:  European J Org Chem       Date:  2011-07-01

8.  Mechanistic analysis and optimization of the copper-catalyzed enantioselective intramolecular alkene aminooxygenation.

Authors:  Monissa C Paderes; Jerome B Keister; Sherry R Chemler
Journal:  J Org Chem       Date:  2012-12-28       Impact factor: 4.354

9.  Methods for direct alkene diamination, new & old.

Authors:  Sam de Jong; Daniel G Nosal; Duncan J Wardrop
Journal:  Tetrahedron       Date:  2012-03-21       Impact factor: 2.457

10.  Synthesis of vicinal aminoalcohols by stereoselective aza-Wacker cyclizations: access to (-)-acosamine by redox relay.

Authors:  Adam B Weinstein; David P Schuman; Zhi Xu Tan; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-17       Impact factor: 15.336

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