Literature DB >> 26663806

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

Aakarsh Saxena1, Felix Perez1, Michael J Krische2.   

Abstract

Ruthenium(0) complexes modified by CyJohnPhos or RuPhos catalyze the successive C-C coupling of acetylenic aldehydes with α-ketols to form [4+2] cycloadducts as single diastereomers. This method enables convergent construction of type II polyketide ring systems of the angucycline class.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  cycloaddition; hydrogenation; natural products; polyketides; ruthenium

Mesh：

Substances：

Year:  2015        PMID： 26663806      PMCID： PMC4718903          DOI： 10.1002/anie.201509646

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


  57 in total

1.  PdCl(2)-catalyzed domino reactions of 2-alkynylbenzaldehydes with indoles: synthesis of fluorescent 5h-benzo[b]carbazol-6-yl ketones.

Authors:  Ri-Yuan Tang; Jin-Heng Li
Journal:  Chemistry       Date:  2010-04-26       Impact factor: 5.236

2.  Tuning the reactivity of Au-complexes in an Au(I)/chiral Brønsted acid cooperative catalytic system: an approach to optically active fused 1,2-dihydroisoquinolines.

Authors:  Nitin T Patil; Anil Kumar Mutyala; Ashok Konala; Ramesh Babu Tella
Journal:  Chem Commun (Camb)       Date:  2012-02-17       Impact factor: 6.222

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

Authors:  Abbas Hassan; Michael J Krische
Journal:  Org Process Res Dev       Date:  2011-11-18       Impact factor: 3.317

4.  AuBr3- and Cu(OTf)2-catalyzed intramolecular [4 + 2] cycloaddition of tethered alkynyl and alkenyl enynones and enynals: a new synthetic method for functionalized polycyclic hydrocarbons.

Authors:  Naoki Asao; Kenichiro Sato; Yoshinori Yamamoto
Journal:  J Org Chem       Date:  2005-04-29       Impact factor: 4.354

5.  Silver-catalyzed domino hydroarylation/cycloisomerization reactions of ortho-alkynylbenzaldehydes: an entry to functionalized isochromene derivatives.

Authors:  Gaëlle Mariaule; Gregory Newsome; Patrick Y Toullec; Philippe Belmont; Véronique Michelet
Journal:  Org Lett       Date:  2014-08-18       Impact factor: 6.005

6.  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

7.  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

8.  Lewis acid-catalyzed benzannulation via unprecedented [4+2] cycloaddition of o-alkynyl(oxo)benzenes and enynals with alkynes.

Authors:  Naoki Asao; Tsutomu Nogami; Sunyoung Lee; Yoshinori Yamamoto
Journal:  J Am Chem Soc       Date:  2003-09-10       Impact factor: 15.419

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.  Mild regiospecific synthesis of 1-alkoxy-isochromenes catalyzed by well-defined [silver(I)(pyridine-containing ligand)] complexes.

Authors:  Monica Dell'Acqua; Brunilde Castano; Clara Cecchini; Tommaso Pedrazzini; Valentina Pirovano; Elisabetta Rossi; Alessandro Caselli; Giorgio Abbiati
Journal:  J Org Chem       Date:  2014-03-31       Impact factor: 4.354
View more
  9 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.  Mechanisms for nickel(0)/N-heterocyclic carbene-catalyzed intramolecular alkene hydroacylation: insights from a DFT study.

Authors:  Qingxi Meng; Fen Wang
Journal:  J Mol Model       Date:  2016-12-21       Impact factor: 1.810

3.  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 4.  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 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

8.  Reaction of FcC[triple bond, length as m-dash]CC(O)R (Fc = ferrocenyl) with Ru3(CO)12 leading to unexpected nitro-group reduced ruthenoles and 1,2-CO-inserted triruthenium clusters.

Authors:  Lei Xu; Liping Jiang; Shasha Li; Guofang Zhang; Weiqiang Zhang; Ziwei Gao
Journal:  RSC Adv       Date:  2018-07-16       Impact factor: 4.036

9.  A thiocyanopalladation/carbocyclization transformation identified through enzymatic screening: stereocontrolled tandem C-SCN and C-C bond formation.

Authors:  G Malik; R A Swyka; V K Tiwari; X Fei; G A Applegate; D B Berkowitz
Journal:  Chem Sci       Date:  2017-10-03       Impact factor: 9.825
  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.