Literature DB >> 28941001

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

Hiroki Sato1, Keisuke Fukaya1, Binit Sharma Poudel1, Michael J Krische1.   

Abstract

Highly exo-selective ruthenium(0) catalyzed transfer hydrogenative cycloadditions of 1,2-diols with cyclohexadiene or norbornadiene are described. Novel bridged bicyclic ring systems are accessible from the diol, α-ketol or 1,2-dione oxidation levels with complete control of diastereoselectivity.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−C bond formation; cycloaddition; diols; hydrogen transfer; ruthenium

Year:  2017        PMID： 28941001      PMCID： PMC5677533          DOI： 10.1002/anie.201708189

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


  39 in total

1.  Transition Metal-Mediated Cycloaddition Reactions.

Authors:  Mark Lautens; Wolfgang Klute; William Tam
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

Review 2.  Oxidative Coupling between Two Hydrocarbons: An Update of Recent C-H Functionalizations.

Authors:  Chao Liu; Jiwen Yuan; Meng Gao; Shan Tang; Wu Li; Renyi Shi; Aiwen Lei
Journal:  Chem Rev       Date:  2015-11-11       Impact factor: 60.622

3.  Ruthenium-catalyzed intramolecular homo-diels-alder reaction of alkyne-tethered norbornadienes. An entry to fused angular triquinanes.

Authors:  Alphonse Tenaglia; Sylvain Gaillard
Journal:  Org Lett       Date:  2007-08-03       Impact factor: 6.005

4.  Cobalt-catalyzed diastereoselective reductive [3 + 2] cycloaddition of allenes and enones.

Authors:  Hong-Tai Chang; Thiruvellore Thatai Jayanth; Chien-Hong Cheng
Journal:  J Am Chem Soc       Date:  2007-03-15       Impact factor: 15.419

5.  Ruthenium-catalyzed homo Diels-Alder [2 + 2 + 2] cycloadditions of alkynyl phosphonates with bicyclo[2.2.1]hepta-2,5-diene.

Authors:  Tanner J Kettles; Neil Cockburn; William Tam
Journal:  J Org Chem       Date:  2011-07-15       Impact factor: 4.354

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

Authors:  Matthias Bender; Ben W H Turnbull; Brett R Ambler; Michael J Krische
Journal:  Science       Date:  2017-08-25       Impact factor: 47.728

7.  Molecular complexity via C-H activation: a dehydrogenative Diels-Alder reaction.

Authors:  Erik M Stang; M Christina White
Journal:  J Am Chem Soc       Date:  2011-09-01       Impact factor: 15.419

8.  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

9.  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

10.  Ruthenium-catalyzed hydrohydroxyalkylation of acrylates with diols and α-hydroxycarbonyl compounds to form spiro- and α-methylene-γ-butyrolactones.

Authors:  Emma L McInturff; Jeffrey Mowat; Andrew R Waldeck; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-11-05       Impact factor: 15.419
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  4 in total

1.  Pyridine(diimine) Iron Diene Complexes Relevant to Catalytic [2+2]-Cycloaddition Reactions.

Authors:  C Rose Kennedy; Hongyu Zhong; Matthew V Joannou; Paul J Chirik
Journal:  Adv Synth Catal       Date:  2019-11-19       Impact factor: 5.837

Review 2.  Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.

Authors:  Michael Holmes; Leyah A Schwartz; Michael J Krische
Journal:  Chem Rev       Date:  2018-06-13       Impact factor: 60.622

3.  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 4.  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
  4 in total

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