Literature DB >> 28839069

Ruthenium-catalyzed insertion of adjacent diol carbon atoms into C-C bonds: Entry to type II polyketides.

Matthias Bender1, Ben W H Turnbull1, Brett R Ambler1, Michael J Krische2.   

Abstract

Current catalytic processes involving carbon-carbon bond activation rely on π-unsaturated coupling partners. Exploiting the concept of transfer hydrogenative coupling, we report a ruthenium(0)-catalyzed cycloaddition of benzocyclobutenones that functionalizes two adjacent saturated diol carbon-hydrogen bonds. These regio- and diastereoselective processes enable convergent construction of type II polyketide substructures.
Copyright © 2017 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works.

Entities:  

Year:  2017        PMID： 28839069      PMCID： PMC5649382          DOI： 10.1126/science.aao0453

Source DB:  PubMed          Journal:  Science        ISSN： 0036-8075            Impact factor:   47.728


  23 in total

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Journal:  Nat Prod Rep       Date:  2011-12-21       Impact factor: 13.423

2.  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

3.  Predictive compound accumulation rules yield a broad-spectrum antibiotic.

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Journal:  Nature       Date:  2017-05-10       Impact factor: 49.962

4.  Nickel-catalyzed intermolecular alkyne insertion into cyclobutanones.

Authors:  Masahiro Murakami; Shinji Ashida; Takanori Matsuda
Journal:  J Am Chem Soc       Date:  2005-05-18       Impact factor: 15.419

5.  Ruthenium catalyzed hydrohydroxyalkylation of isoprene with heteroaromatic secondary alcohols: isolation and reversible formation of the putative metallacycle intermediate.

Authors:  Boyoung Y Park; T Patrick Montgomery; Victoria J Garza; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-10-24       Impact factor: 15.419

6.  A single step approach to piperidines via Ni-catalyzed β-carbon elimination.

Authors:  Puneet Kumar; Janis Louie
Journal:  Org Lett       Date:  2012-04-02       Impact factor: 6.005

7.  Diols, α-Ketols, and Diones as 22π Components in [2+2+2] Cycloadditions of 1,6-Diynes via Ruthenium(0)-Catalyzed Transfer Hydrogenation.

Authors:  Hiroki Sato; Matthias Bender; Weijie Chen; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-12-09       Impact factor: 15.419

8.  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

9.  Direct, redox-neutral prenylation and geranylation of secondary carbinol C-H bonds: C4-regioselectivity in ruthenium-catalyzed C-C couplings of dienes to α-hydroxy esters.

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10.  Synthesis of enantiopure dehydropiperidinones from α-amino acids and alkynes via azetidin-3-ones.

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  9 in total

1.  Diols as Dienophiles: Bridged Carbocycles via Ruthenium(0)-Catalyzed Transfer Hydrogenative Cycloadditions of Cyclohexadiene or Norbornadiene.

Authors:  Hiroki Sato; Keisuke Fukaya; Binit Sharma Poudel; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-10       Impact factor: 15.336

2.  Rapid syntheses of N-fused heterocycles via acyl-transfer in heteroaryl ketones.

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3.  Thermal Hetero-Diels-Alder Reaction of Benzocyclobutenones with Isatins To Form 2-Oxindole Spirolactones.

Authors:  Thomas Wurm; Ben W H Turnbull; Brett R Ambler; Michael J Krische
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4.  A ring expansion strategy towards diverse azaheterocycles.

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Review 5.  Ruthenium(0)-Catalyzed Cycloaddition of 1,2-Diols, Ketols, or Diones via Alcohol-Mediated Hydrogen Transfer.

Authors:  Hiroki Sato; Ben W H Turnbull; Keisuke Fukaya; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2018-02-06       Impact factor: 15.336

6.  Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction.

Authors:  Brett R Ambler; Ben W H Turnbull; Sankar Rao Suravarapu; Maulen M Uteuliyev; Nancy O Huynh; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-07-11       Impact factor: 15.419

Review 7.  Ruthenium-Catalyzed Cycloadditions to Form Five-, Six-, and Seven-Membered Rings.

Authors:  Rosalie S Doerksen; Tomáš Hodík; Guanyu Hu; Nancy O Huynh; William G Shuler; Michael J Krische
Journal:  Chem Rev       Date:  2021-02-12       Impact factor: 60.622

Review 8.  Catalysis with cycloruthenated complexes.

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9.  Dihydroquinazolinones as adaptative C(sp3) handles in arylations and alkylations via dual catalytic C-C bond-functionalization.

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Journal:  Nat Commun       Date:  2022-05-03       Impact factor: 17.694
  9 in total

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