Literature DB >> 29897740

Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.

Michael Holmes1, Leyah A Schwartz1, Michael J Krische1.   

Abstract

Metal-catalyzed reductive coupling has emerged as an alternative to the use of stoichiometric organometallic reagents in an increasingly diverse range of carbonyl and imine additions. In this review, the use of diene, allene, and enyne pronucleophiles in intermolecular carbonyl and imine reductive couplings are surveyed, along with related hydrogen autotransfer processes.

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Year:  2018        PMID： 29897740      PMCID： PMC6203947          DOI： 10.1021/acs.chemrev.8b00213

Source DB:  PubMed          Journal:  Chem Rev        ISSN： 0009-2665            Impact factor:   60.622


  127 in total

1.  Highly enantioselective direct reductive coupling of conjugated alkynes and alpha-ketoesters via rhodium-catalyzed asymmetric hydrogenation.

Authors:  Jong-Rock Kong; Ming-Yu Ngai; Michael J Krische
Journal:  J Am Chem Soc       Date:  2006-01-25       Impact factor: 15.419

2.  A general strategy for regiocontrol in nickel-catalyzed reductive couplings of aldehydes and alkynes.

Authors:  Hasnain A Malik; Grant J Sormunen; John Montgomery
Journal:  J Am Chem Soc       Date:  2010-05-12       Impact factor: 15.419

3.  Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective Methods.

Authors:  Abbas Hassan; Michael J Krische
Journal:  Org Process Res Dev       Date:  2011-11-18       Impact factor: 3.317

4.  Enantioselective Formation of CF3-Bearing All-Carbon Quaternary Stereocenters via C-H Functionalization of Methanol: Iridium Catalyzed Allene Hydrohydroxymethylation.

Authors:  Michael Holmes; Khoa D Nguyen; Leyah A Schwartz; Tom Luong; Michael J Krische
Journal:  J Am Chem Soc       Date:  2017-06-12       Impact factor: 15.419

5.  Nickel-catalyzed intermolecular coupling of 1,3-dienes and aldehydes via transmetalation of nickelacycles with diisobutylaluminum acetylacetonate.

Authors:  Yoshihiro Sato; Rieko Sawaki; Nozomi Saito; Miwako Mori
Journal:  J Org Chem       Date:  2002-02-08       Impact factor: 4.354

6.  Ruthenium(II)-catalyzed regioselective reductive coupling of α-imino esters with dienes.

Authors:  Shujie Zhu; Xiaoxia Lu; Yueting Luo; Wei Zhang; Huanfeng Jiang; Ming Yan; Wei Zeng
Journal:  Org Lett       Date:  2013-03-15       Impact factor: 6.005

7.  Successive C-C coupling of dienes to vicinally dioxygenated hydrocarbons: ruthenium catalyzed [4 + 2] cycloaddition across the diol, hydroxycarbonyl, or dione oxidation levels.

Authors:  Laina M Geary; Ben W Glasspoole; Mary M Kim; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-02-28       Impact factor: 15.419

8.  Enantioselective reductive coupling of 1,3-enynes to glyoxalates mediated by hydrogen: asymmetric synthesis of beta,gamma-unsaturated alpha-hydroxy esters.

Authors:  Young-Taek Hong; Chang-Woo Cho; Eduardas Skucas; Michael J Krische
Journal:  Org Lett       Date:  2007-08-18       Impact factor: 6.005

9.  Diastereo- and enantioselective reactions of bis(pinacolato)diboron, 1,3-enynes, and aldehydes catalyzed by an easily accessible bisphosphine-Cu complex.

Authors:  Fanke Meng; Fredrik Haeffner; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2014-08-04       Impact factor: 15.419

10.  Ni-catalyzed homoallylation of polyhydroxy n,o-acetals with conjugated dienes promoted by triethylborane.

Authors:  Takamichi Mori; Yusuke Akioka; Gen Onodera; Masanari Kimura
Journal:  Molecules       Date:  2014-07-02       Impact factor: 4.411
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  62 in total

Review 1.  Engaging Aldehydes in CuH-Catalyzed Reductive Coupling Reactions: Stereoselective Allylation with Unactivated 1,3-Diene Pronucleophiles.

Authors:  Chengxi Li; Kwangmin Shin; Richard Y Liu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-22       Impact factor: 15.336

2.  Direct Conversion of Primary Alcohols to 1,2-Amino Alcohols: Enantioselective Iridium-Catalyzed Carbonyl Reductive Coupling of Phthalimido-Allene via Hydrogen Auto-Transfer.

Authors:  Kim Spielmann; Ming Xiang; Leyah A Schwartz; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-08-29       Impact factor: 15.419

3.  Inversion of Enantioselectivity in Allene Gas versus Allyl Acetate Reductive Aldehyde Allylation Guided by Metal-Centered Stereogenicity: An Experimental and Computational Study.

Authors:  Seung Wook Kim; Cole C Meyer; Binh Khanh Mai; Peng Liu; Michael J Krische
Journal:  ACS Catal       Date:  2019-09-11       Impact factor: 13.084

4.  Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and Beyond.

Authors:  Kelvin Pak Shing Cheung; Daria Kurandina; Tetsuji Yata; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2020-05-19       Impact factor: 15.419

5.  CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition.

Authors:  Richard Y Liu; Stephen L Buchwald
Journal:  Acc Chem Res       Date:  2020-05-13       Impact factor: 22.384

6.  CuH-Catalyzed Enantioselective Ketone Allylation with 1,3-Dienes: Scope, Mechanism, and Applications.

Authors:  Chengxi Li; Richard Y Liu; Luke T Jesikiewicz; Yang Yang; Peng Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2019-03-12       Impact factor: 15.419

7.  Vinyl Triflate-Aldehyde Reductive Coupling-Redox Isomerization Mediated by Formate: Rhodium-Catalyzed Ketone Synthesis in the Absence of Stoichiometric Metals.

Authors:  William G Shuler; Robert A Swyka; Tabitha T Schempp; Brian J Spinello; Michael J Krische
Journal:  Chemistry       Date:  2019-09-04       Impact factor: 5.236

Review 8.  Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis.

Authors:  Rosalie S Doerksen; Cole C Meyer; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-26       Impact factor: 15.336

9.  Rhodium-Catalyzed Aldehyde Arylation via Formate-Mediated Transfer Hydrogenation: Beyond Metallic Reductants in Grignard/Nozaki-Hiyami-Kishi-Type Addition.

Authors:  Robert A Swyka; Wandi Zhang; Jeffery Richardson; J Craig Ruble; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-01-29       Impact factor: 15.419

10.  Diastereo-, Enantio-, and anti-Selective Formation of Secondary Alcohol and Quaternary Carbon Stereocenters by Cu-Catalyzed Additions of B-Substituted Allyl Nucleophiles to Carbonyls.

Authors:  Emilie Wheatley; Joseph M Zanghi; Simon J Meek
Journal:  Org Lett       Date:  2020-11-18       Impact factor: 6.005
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