Literature DB >> 19040235

Catalytic carbonyl addition through transfer hydrogenation: a departure from preformed organometallic reagents.

John F Bower1, In Su Kim, Ryan L Patman, Michael J Krische.   

Abstract

Classical protocols for carbonyl allylation, propargylation and vinylation typically rely upon the use of preformed allyl metal, allenyl metal and vinyl metal reagents, respectively, mandating stoichiometric generation of metallic byproducts. Through transfer hydrogenative C-C coupling, however, carbonyl addition may be achieved from the aldehyde or alcohol oxidation level in the absence of stoichiometric organometallic reagents or metallic reductants. Here, we review transfer hydrogenative methods for carbonyl addition, which encompass the first catalytic protocols enabling direct C-H functionalization of alcohols.

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Year:  2009        PMID: 19040235      PMCID: PMC2775511          DOI: 10.1002/anie.200802938

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


  86 in total

Review 1.  Non-metathesis ruthenium-catalyzed C-C bond formation.

Authors:  B M Trost; F D Toste; A B Pinkerton
Journal:  Chem Rev       Date:  2001-07       Impact factor: 60.622

2.  [2,2]paracyclophane-based N,O-ligands in alkenylzinc additions to aldehydes.

Authors:  S Dahmen; S Bräse
Journal:  Org Lett       Date:  2001-12-13       Impact factor: 6.005

3.  Strained silacycles in organic synthesis: a new reagent for the enantioselective allylation of aldehydes.

Authors:  James W A Kinnaird; Pui Yee Ng; Katsumi Kubota; Xiaolun Wang; James L Leighton
Journal:  J Am Chem Soc       Date:  2002-07-10       Impact factor: 15.419

4.  Hydrogen-mediated aldol reductive coupling of vinyl ketones catalyzed by rhodium: high syn-selectivity through the effect of tri-2-furylphosphine.

Authors:  Cheol-Kyu Jung; Susan A Garner; Michael J Krische
Journal:  Org Lett       Date:  2006-02-02       Impact factor: 6.005

Review 5.  Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular catalysts.

Authors:  Takao Ikariya; A John Blacker
Journal:  Acc Chem Res       Date:  2007-10-26       Impact factor: 22.384

6.  First catalytic allyltitanation reactions.

Authors:  Laurianne Bareille; Pierre Le Gendre; Claude Moïse
Journal:  Chem Commun (Camb)       Date:  2004-12-21       Impact factor: 6.222

7.  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

8.  Novel applications of alkenyl zirconocenes.

Authors:  Peter Wipf; Christopher Kendall
Journal:  Chemistry       Date:  2002-04-15       Impact factor: 5.236

9.  Catalytic asymmetric reductive coupling of alkynes and aldehydes: enantioselective synthesis of allylic alcohols and alpha-hydroxy ketones.

Authors:  Karen M Miller; Wei-Sheng Huang; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2003-03-26       Impact factor: 15.419

10.  Allylation of alcohols and carboxylic acids with allyl acetate catalyzed by [Ir(cod)2](+)BF4- complex.

Authors:  Hideto Nakagawa; Tomotaka Hirabayashi; Satoshi Sakaguchi; Yasutaka Ishii
Journal:  J Org Chem       Date:  2004-05-14       Impact factor: 4.354

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  69 in total

1.  Allenamide hydro-hydroxyalkylation: 1,2-amino alcohols via ruthenium-catalyzed carbonyl anti-aminoallylation.

Authors:  Jason R Zbieg; Emma L McInturff; Michael J Krische
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

Review 2.  Asymmetric Iridium-Catalyzed C-C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition.

Authors:  Inji Shin; Michael J Krische
Journal:  Top Curr Chem       Date:  2016

3.  Direct generation of acyclic polypropionate stereopolyads via double diastereo- and enantioselective iridium-catalyzed crotylation of 1,3-diols: beyond stepwise carbonyl addition in polyketide construction.

Authors:  Xin Gao; Hoon Han; Michael J Krische
Journal:  J Am Chem Soc       Date:  2011-07-25       Impact factor: 15.419

4.  Catalytic asymmetric carbon-carbon bond formation using alkenes as alkylmetal equivalents.

Authors:  Rebecca M Maksymowicz; Philippe M C Roth; Stephen P Fletcher
Journal:  Nat Chem       Date:  2012-07-15       Impact factor: 24.427

5.  Formation of C-C bonds via ruthenium-catalyzed transfer hydrogenation().

Authors:  Joseph Moran; Michael J Krische
Journal:  Pure Appl Chem       Date:  2012-03-13       Impact factor: 2.453

6.  Consecutive iridium catalyzed C-C and C-H bond forming hydrogenations for the diastereo- and enantioselective synthesis of syn-3-fluoro-1-alcohols: C-H (2-fluoro)allylation of primary alcohols.

Authors:  Abbas Hassan; T Patrick Montgomery; Michael J Krische
Journal:  Chem Commun (Camb)       Date:  2012-04-04       Impact factor: 6.222

7.  A Radical Approach to Anionic Chemistry: Synthesis of Ketones, Alcohols, and Amines.

Authors:  Shengyang Ni; Natalia M Padial; Cian Kingston; Julien C Vantourout; Daniel C Schmitt; Jacob T Edwards; Monika M Kruszyk; Rohan R Merchant; Pavel K Mykhailiuk; Brittany B Sanchez; Shouliang Yang; Matthew A Perry; Gary M Gallego; James J Mousseau; Michael R Collins; Robert J Cherney; Pavlo S Lebed; Jason S Chen; Tian Qin; Phil S Baran
Journal:  J Am Chem Soc       Date:  2019-04-16       Impact factor: 15.419

8.  Enantioselective allylation, crotylation, and reverse prenylation of substituted isatins: iridium-catalyzed C-C bond-forming transfer hydrogenation.

Authors:  Junji Itoh; Soo Bong Han; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

Review 9.  Axial preferences in allylation reactions via the Zimmerman-Traxler transition state.

Authors:  Tom Mejuch; Noga Gilboa; Eric Gayon; Hao Wang; K N Houk; Ilan Marek
Journal:  Acc Chem Res       Date:  2013-05-14       Impact factor: 22.384

10.  Tunable Phosphoramidite Ligands for Asymmetric Hydrovinylation: Ligands par excellence for Generation of All-Carbon Quaternary Centers.

Authors:  Craig R Smith; Hwan Jung Lim; Aibin Zhang; T V Rajanbabu
Journal:  Synthesis (Stuttg)       Date:  2009-01-01       Impact factor: 3.157

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