Literature DB >> 25938947

Ruthenium(0) Catalyzed Endiyne-α-Ketol [4 + 2] Cycloaddition: Convergent Assembly of Type II Polyketide Substructures via C-C Bond Forming Transfer Hydrogenation.

Aakarsh Saxena1, Felix Perez1, Michael J Krische1.   

Abstract

Upon exposure of 3,4-benzannulated 1,5-diynes (benzo-endiynes) to α-ketols (α-hydroxyketones) in the presence of Ru(0) catalysts derived from Ru3(CO)12 and RuPhos or CyJohnPhos, successive redox-triggered C-C coupling occurs to generate products of [4 + 2] cycloaddition. The proposed catalytic mechanism involves consecutive alkyne-carbonyl oxidative couplings to form transient oxaruthanacycles that suffer α-ketol mediated transfer hydrogenolysis. This process provides a new, convergent means of assembling Type II polyketide substructures.

Entities:  

Mesh：

Substances：

Year:  2015        PMID： 25938947      PMCID： PMC4470559          DOI： 10.1021/jacs.5b02755

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  59 in total

1.  Regio- and diastereoselective C-C coupling of α-olefins and styrenes to 3-hydroxy-2-oxindoles by Ru-catalyzed hydrohydroxyalkylation.

Authors:  Eiji Yamaguchi; Jeffrey Mowat; Tom Luong; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-05       Impact factor: 15.336

2.  Synthetic development and mechanistic study on Pd(II)-catalyzed cyclization of enediynes to benzo[a]carbazoles.

Authors:  Chin-Chau Chen; Lin-Yu Chin; Shyh-Chyun Yang; Ming-Jung Wu
Journal:  Org Lett       Date:  2010-11-18       Impact factor: 6.005

3.  Total synthesis of isokidamycin.

Authors:  B Michael O'Keefe; Douglas M Mans; David E Kaelin; Stephen F Martin
Journal:  J Am Chem Soc       Date:  2010-11-10       Impact factor: 15.419

4.  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

5.  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.

Authors:  Joyce C Leung; Laina M Geary; Te-Yu Chen; Jason R Zbieg; Michael J Krische
Journal:  J Am Chem Soc       Date:  2012-09-17       Impact factor: 15.419

6.  Gold vinylidene complexes: intermolecular C(sp3)-H insertions and cyclopropanations pathways.

Authors:  A Stephen K Hashmi; Marcel Wieteck; Ingo Braun; Matthias Rudolph; Frank Rominger
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-17       Impact factor: 15.336

7.  Gold(I)-catalyzed regioselective inter-/intramolecular addition cascade of di- and triynes for direct construction of substituted naphthalenes.

Authors:  Saori Naoe; Yamato Suzuki; Kimio Hirano; Yusuke Inaba; Shinya Oishi; Nobutaka Fujii; Hiroaki Ohno
Journal:  J Org Chem       Date:  2012-05-15       Impact factor: 4.354

8.  Platinum- and gold-catalyzed hydrative carbocyclization of oxo diynes for one-pot synthesis of benzopyrones and bicyclic spiro ketones.

Authors:  Arindam Das; Hsu-Kai Chang; Cheng-Hua Yang; Rai-Shung Liu
Journal:  Org Lett       Date:  2008-08-23       Impact factor: 6.005

9.  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

10.  Redox-triggered C-C coupling of alcohols and vinyl epoxides: diastereo- and enantioselective formation of all-carbon quaternary centers via tert-(hydroxy)-prenylation.

Authors:  Jiajie Feng; Victoria J Garza; Michael J Krische
Journal:  J Am Chem Soc       Date:  2014-06-10       Impact factor: 15.419
View more
  7 in total

1.  Osmium(0)-Catalyzed C-C Coupling of Ethylene and α-Olefins with Diols, Ketols, or Hydroxy Esters via Transfer Hydrogenation.

Authors:  Boyoung Y Park; Tom Luong; Hiroki Sato; Michael J Krische
Journal:  J Org Chem       Date:  2016-09-08       Impact factor: 4.354

2.  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

Review 3.  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

Review 4.  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

5.  Ruthenium(0)-Catalyzed [4+2] Cycloaddition of Acetylenic Aldehydes with α-Ketols: Convergent Construction of Angucycline Ring Systems.

Authors:  Aakarsh Saxena; Felix Perez; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-09       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
  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.