Literature DB >> 26661678

Copper Hydride Catalyzed Hydroamination of Alkenes and Alkynes.

Michael T Pirnot1, Yi-Ming Wang1, Stephen L Buchwald2.   

Abstract

Over the past few years, CuH-catalyzed hydroamination has been discovered and developed as a robust and conceptually novel approach for the synthesis of enantioenriched secondary and tertiary amines. The success in this area of research was made possible through the large body of precedent in copper(I) hydride catalysis and the well-explored use of hydroxylamine esters as electrophilic amine sources in related copper-catalyzed processes. This Minireview details the background, advances, and mechanistic investigations in CuH-catalyzed hydroamination.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; chiral amine synthesis; copper catalysis; copper(I) hydride; hydroamination

Mesh:

Substances:

Year:  2015        PMID: 26661678      PMCID: PMC4782926          DOI: 10.1002/anie.201507594

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  53 in total

1.  Ligand-accelerated, copper-catalyzed asymmetric hydrosilylations of aryl ketones.

Authors:  B H Lipshutz; K Noson; W Chrisman
Journal:  J Am Chem Soc       Date:  2001-12-26       Impact factor: 15.419

2.  Copper(I)-catalyzed asymmetric hydrosilylations of imines at ambient temperatures.

Authors:  Bruce H Lipshutz; Hideo Shimizu
Journal:  Angew Chem Int Ed Engl       Date:  2004-04-19       Impact factor: 15.336

3.  Stable reagents for the generation of N-centered radicals: hydroamination of norbornene.

Authors:  Jens Kemper; Armido Studer
Journal:  Angew Chem Int Ed Engl       Date:  2005-08-05       Impact factor: 15.336

4.  Dynamic kinetic resolution via asymmetric conjugate reduction: enantio- and diastereoselective synthesis of 2,4-dialkyl cyclopentanones.

Authors:  Valdas Jurkauskas; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2002-03-27       Impact factor: 15.419

5.  One-pot synthesis of enantiomerically enriched 2,3-disubstituted cyclopentanones via copper-catalyzed 1,4-reduction and alkylation.

Authors:  J Yun; S L Buchwald
Journal:  Org Lett       Date:  2001-04-19       Impact factor: 6.005

6.  Brønsted acid-catalyzed intramolecular hydroamination of protected alkenylamines. Synthesis of pyrrolidines and piperidines.

Authors:  Björn Schlummer; John F Hartwig
Journal:  Org Lett       Date:  2002-05-02       Impact factor: 6.005

7.  Asymmetric hydrosilylation of aryl ketones catalyzed by copper hydride complexed by nonracemic biphenyl bis-phosphine ligands.

Authors:  Bruce H Lipshutz; Kevin Noson; Will Chrisman; Asher Lower
Journal:  J Am Chem Soc       Date:  2003-07-23       Impact factor: 15.419

8.  Organolanthanide-catalyzed hydroamination.

Authors:  Sukwon Hong; Tobin J Marks
Journal:  Acc Chem Res       Date:  2004-09       Impact factor: 22.384

9.  Copper-catalyzed electrophilic amination of diorganozinc reagents.

Authors:  Ashley M Berman; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2004-05-12       Impact factor: 15.419

10.  Copper-catalyzed asymmetric conjugate reduction as a route to novel beta-azaheterocyclic acid derivatives.

Authors:  Matthew P Rainka; Yimon Aye; Stephen L Buchwald
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-05       Impact factor: 11.205

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  67 in total

1.  Enantioselective Synthesis of β-Amino Acid Derivatives Enabled by Ligand-Controlled Reversal of Hydrocupration Regiochemistry.

Authors:  Sheng Guo; Jiaqi Zhu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-11       Impact factor: 15.336

2.  A Modified System for the Synthesis of Enantioenriched N-Arylamines through Copper-Catalyzed Hydroamination.

Authors:  Saki Ichikawa; Shaolin Zhu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-12       Impact factor: 15.336

3.  Catalytic Alkyne Arylation Using Traceless Directing Groups.

Authors:  Jung-Woo Park; Bubwoong Kang; Vy M Dong
Journal:  Angew Chem Int Ed Engl       Date:  2018-09-11       Impact factor: 15.336

4.  Enantioselective Markovnikov Addition of Carbamates to Allylic Alcohols for the Construction of α-Secondary and α-Tertiary Amines.

Authors:  Ana Bahamonde; Buthainah Al Rifaie; Victor Martín-Heras; Jamie R Allen; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2019-05-24       Impact factor: 15.419

Review 5.  Cross-Coupling of Heteroatomic Electrophiles.

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

6.  Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates.

Authors:  Yujing Zhou; Jeffrey S Bandar; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2017-06-06       Impact factor: 15.419

7.  Nickel-Catalyzed Dearomative trans-1,2-Carboamination.

Authors:  Lucas W Hernandez; Ulrich Klöckner; Jola Pospech; Lilian Hauss; David Sarlah
Journal:  J Am Chem Soc       Date:  2018-03-23       Impact factor: 15.419

8.  Copper-Catalyzed Enantioselective Hydroamination of Alkenes.

Authors:  Richard Y Liu; Stephen L Buchwald
Journal:  Organic Synth       Date:  2018

9.  Strategies for the Catalytic Enantioselective Synthesis of α-Trifluoromethyl Amines.

Authors:  Chibueze I Onyeagusi; Steven J Malcolmson
Journal:  ACS Catal       Date:  2020-10-12       Impact factor: 13.084

10.  A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes.

Authors:  Erica Y Tsai; Richard Y Liu; Yang Yang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-02-02       Impact factor: 15.419

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