Literature DB >> 22125398

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

Abbas Hassan1, Michael J Krische.   

Abstract

Hydrogenation of π-unsaturated reactants in the presence of carbonyl compounds or imines promotes reductive C-C coupling, providing a byproduct-free alternative to stoichiometric organometallic reagents in an ever-increasing range of C=X (X = O, NR) additions. Under transfer hydrogenation conditions, hydrogen exchange between alcohols and π-unsaturated reactants triggers generation of electrophile-nucleophile pairs, enabling carbonyl addition directly from the alcohol oxidation level, bypassing discrete alcohol oxidation and generation of stoichiometric byproducts.

Entities:  

Year:  2011        PMID: 22125398      PMCID: PMC3224080          DOI: 10.1021/op200195m

Source DB:  PubMed          Journal:  Org Process Res Dev        ISSN: 1083-6160            Impact factor:   3.317


  45 in total

Review 1.  High-throughput and parallel screening methods in asymmetric hydrogenation.

Authors:  Christoph Jäkel; Rocco Paciello
Journal:  Chem Rev       Date:  2006-07       Impact factor: 60.622

2.  Hydrogen-mediated C-C bond formation: a broad new concept in catalytic C-C coupling.

Authors:  Ming-Yu Ngai; Jong-Rock Kong; Michael J Krische
Journal:  J Org Chem       Date:  2007-02-16       Impact factor: 4.354

3.  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

4.  Mechanism and stereoselectivity of asymmetric hydrogenation.

Authors:  J Halpern
Journal:  Science       Date:  1982-07-30       Impact factor: 47.728

5.  Alpha-hydroxy esters via enantioselective hydrogen-mediated C-C coupling: regiocontrolled reactions of silyl-substituted 1,3-diynes.

Authors:  Chang-Woo Cho; Michael J Krische
Journal:  Org Lett       Date:  2006-08-17       Impact factor: 6.005

6.  Hydrogen-mediated reductive coupling of conjugated alkynes with ethyl (N-Sulfinyl)iminoacetates: synthesis of unnatural alpha-amino acids via rhodium-catalyzed C-C bond forming hydrogenation.

Authors:  Jong-Rock Kong; Chang-Woo Cho; Michael J Krische
Journal:  J Am Chem Soc       Date:  2005-08-17       Impact factor: 15.419

7.  Formation of C-C Bonds via Ruthenium Catalyzed Transfer Hydrogenation: Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level.

Authors:  Fumitoshi Shibahara; Michael J Krische
Journal:  Chem Lett       Date:  2008       Impact factor: 1.389

Review 8.  From a chiral switch to a ligand portfolio for asymmetric catalysis.

Authors:  Hans-Ulrich Blaser; Benoît Pugin; Felix Spindler; Marc Thommen
Journal:  Acc Chem Res       Date:  2007-08-24       Impact factor: 22.384

9.  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

10.  Catalyst-directed diastereoselectivity in hydrogenative couplings of acetylene to alpha-chiral aldehydes: formal synthesis of all eight L-hexoses.

Authors:  Soo Bong Han; Jong Rock Kong; Michael J Krische
Journal:  Org Lett       Date:  2008-08-26       Impact factor: 6.005

View more
  61 in total

1.  Enantioselective conversion of primary alcohols to α-exo-methylene γ-butyrolactones via iridium-catalyzed C-C bond-forming transfer hydrogenation: 2-(alkoxycarbonyl)allylation.

Authors:  T Patrick Montgomery; Abbas Hassan; Boyoung Y Park; Michael J Krische
Journal:  J Am Chem Soc       Date:  2012-06-26       Impact factor: 15.419

2.  Reductive Cyclization of Halo-Ketones to Form 3-Hydroxy-2-Oxindoles via Palladium Catalyzed Hydrogenation: A Hydrogen-Mediated Grignard Addition.

Authors:  Inji Shin; Stephen D Ramgren; Michael J Krische
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

3.  Modular Terpenoid Construction via Catalytic Enantioselective Formation of All-Carbon Quaternary Centers: Total Synthesis of Oridamycin A, Triptoquinones B and C, and Isoiresin.

Authors:  Jiajie Feng; Florian Noack; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-09-15       Impact factor: 15.419

4.  Total Synthesis of Swinholide A: An Exposition in Hydrogen-Mediated C-C Bond Formation.

Authors:  Inji Shin; Suckchang Hong; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-10-25       Impact factor: 15.419

5.  A Metallacycle Fragmentation Strategy for Vinyl Transfer from Enol Carboxylates to Secondary Alcohol C-H Bonds via Osmium- or Ruthenium-Catalyzed Transfer Hydrogenation.

Authors:  Boyoung Y Park; Tom Luong; Hiroki Sato; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-06-12       Impact factor: 15.419

6.  Enantioselective C-H crotylation of primary alcohols via hydrohydroxyalkylation of butadiene.

Authors:  Jason R Zbieg; Eiji Yamaguchi; Emma L McInturff; Michael J Krische
Journal:  Science       Date:  2012-03-22       Impact factor: 47.728

7.  Reductive C-C Coupling via Hydrogenation and Transfer Hydrogenation: Departure from Stoichiometric Metals in Carbonyl Addition.

Authors:  James Roane; Michael Holmes; Michael J Krische
Journal:  Curr Opin Green Sustain Chem       Date:  2017-06-09

Review 8.  Ruthenium-Catalyzed Transfer Hydrogenation for C-C Bond Formation: Hydrohydroxyalkylation and Hydroaminoalkylation via Reactant Redox Pairs.

Authors:  Felix Perez; Susumu Oda; Laina M Geary; Michael J Krische
Journal:  Top Curr Chem (Cham)       Date:  2016-05-30

9.  Total synthesis of cyanolide A in the absence of protecting groups, chiral auxiliaries, or premetalated carbon nucleophiles.

Authors:  Andrew R Waldeck; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2013-03-11       Impact factor: 15.336

10.  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

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.