Literature DB >> 24554613

Catalytic, enantioselective synthesis of 1,2-anti-diols by asymmetric ring-opening/cross-metathesis.

John Hartung1, Robert H Grubbs.   

Abstract

An enantioselective method for the synthesis of 1,2-anti-diols has been developed. A cyclometalated chiral-at-ruthenium complex catalyzes the asymmetric ring-opening/cross-metathesis of dioxygenated cyclobutenes, thus resulting in functionally rich synthetic building blocks. Syntheses of the insect pheromone (+)-endo-brevicomin and monosaccharide ribose demonstrate the synthetic utility of the 1,2-anti-diol fragments generated in the title reaction.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alcohols; asymmetric catalysis; metathesis; pheromones; ruthenium

Mesh：

Substances：

Year:  2014        PMID： 24554613      PMCID： PMC4037230          DOI： 10.1002/anie.201310767

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


  36 in total

1.  Desymmetrization by ring-closing metathesis leading to 6,8-dioxabicyclo[3.2.1]octanes: a new route for the synthesis of (+)-exo- and endo-brevicomin.

Authors:  S D Burke; N Müller; C M Beaudry
Journal:  Org Lett       Date:  1999-12-02       Impact factor: 6.005

2.  Enol ethers as substrates for efficient Z- and enantioselective ring-opening/cross-metathesis reactions promoted by stereogenic-at-Mo complexes: utility in chemical synthesis and mechanistic attributes.

Authors:  Miao Yu; Ismail Ibrahem; Masayuki Hasegawa; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2012-01-24       Impact factor: 15.419

3.  Teaching metathesis "simple" stereochemistry.

Authors:  Alois Fürstner
Journal:  Science       Date:  2013-09-20       Impact factor: 47.728

4.  A novel ligand for the enantioselective ruthenium-catalyzed olefin metathesis.

Authors:  Axel Kannenberg; Daniel Rost; Stefan Eibauer; Sascha Tiede; Siegfried Blechert
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-28       Impact factor: 15.336

5.  Cross-metathesis/iridium(I)-catalyzed allylic etherification strategy: (iterative) catalytic asymmetric synthesis of syn- and anti-1,2-diols.

Authors:  Dongeun Kim; Jae Seung Lee; Suk Bin Kong; Hyunsoo Han
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-15       Impact factor: 15.336

6.  Synthesis, isolation, characterization, and reactivity of high-energy stereogenic-at-Ru carbenes: stereochemical inversion through olefin metathesis and other pathways.

Authors:  R Kashif M Khan; Adil R Zhugralin; Sebastian Torker; Robert V O'Brien; Pamela J Lombardi; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2012-07-20       Impact factor: 15.419

7.  Asymmetric synthesis of gamma-hydroxy alpha,beta-unsaturated aldehydes via enantioselective direct addition of propargyl acetate to aldehydes.

Authors:  E El-Sayed; N K Anand; E M Carreira
Journal:  Org Lett       Date:  2001-09-20       Impact factor: 6.005

8.  Enantioselective silyl protection of alcohols catalysed by an amino-acid-based small molecule.

Authors:  Yu Zhao; Jason Rodrigo; Amir H Hoveyda; Marc L Snapper
Journal:  Nature       Date:  2006-09-07       Impact factor: 49.962

9.  Highly active chiral ruthenium catalysts for asymmetric ring-closing olefin metathesis.

Authors:  Timothy W Funk; Jacob M Berlin; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2006-02-15       Impact factor: 15.419

10.  Catalytic Z-selective olefin cross-metathesis for natural product synthesis.

Authors:  Simon J Meek; Robert V O'Brien; Josep Llaveria; Richard R Schrock; Amir H Hoveyda
Journal:  Nature       Date:  2011-03-24       Impact factor: 49.962
View more
  9 in total

1.  High-value alcohols and higher-oxidation-state compounds by catalytic Z-selective cross-metathesis.

Authors:  Ming Joo Koh; R Kashif M Khan; Sebastian Torker; Miao Yu; Malte S Mikus; Amir H Hoveyda
Journal:  Nature       Date:  2015-01-08       Impact factor: 49.962

2.  Catalyst-controlled stereoselective olefin metathesis as a principal strategy in multistep synthesis design: a concise route to (+)-neopeltolide.

Authors:  Miao Yu; Richard R Schrock; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-06       Impact factor: 15.336

3.  Tandem Z-Selective Cross-Metathesis/Dihydroxylation: Synthesis of anti-1,2-Diols.

Authors:  Peter K Dornan; Zachary K Wickens; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2015-04-27       Impact factor: 15.336

4.  Enantioselective olefin metathesis with cyclometalated ruthenium complexes.

Authors:  John Hartung; Peter K Dornan; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2014-09-02       Impact factor: 15.419

5.  Mechanism of Olefin Metathesis with Neutral and Cationic Molybdenum Imido Alkylidene N-Heterocyclic Carbene Complexes.

Authors:  Katharina Herz; Maren Podewitz; Laura Stöhr; Dongren Wang; Wolfgang Frey; Klaus R Liedl; Suman Sen; Michael R Buchmeiser
Journal:  J Am Chem Soc       Date:  2019-05-09       Impact factor: 15.419

6.  Nickel-Catalyzed Enantioselective Synthesis of Pre-Differentiated Homoallylic syn- or anti-1,2-Diols from Aldehydes and Dienol Ethers.

Authors:  Thomas Q Davies; John J Murphy; Maxime Dousset; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2021-08-19       Impact factor: 15.419

7.  Evolution of catalytic stereoselective olefin metathesis: from ancillary transformation to purveyor of stereochemical identity.

Authors:  Amir H Hoveyda
Journal:  J Org Chem       Date:  2014-04-10       Impact factor: 4.354

8.  Carboxylate-assisted C(sp³)-H activation in olefin metathesis-relevant ruthenium complexes.

Authors:  Jeffrey S Cannon; Lufeng Zou; Peng Liu; Yu Lan; Daniel J O'Leary; K N Houk; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2014-04-25       Impact factor: 15.419

9.  Cationic ruthenium alkylidene catalysts bearing phosphine ligands.

Authors:  Koji Endo; Robert H Grubbs
Journal:  Dalton Trans       Date:  2016-02-28       Impact factor: 4.390
  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.