Literature DB >> 19967680

Catalytic enantioselective olefin metathesis in natural product synthesis. Chiral metal-based complexes that deliver high enantioselectivity and more.

Amir H Hoveyda1, Steven J Malcolmson, Simon J Meek, Adil R Zhugralin.   

Abstract

Chiral olefin metathesis catalysts enable chemists to access enantiomerically enriched small molecules with high efficiency; synthesis schemes involving such complexes can be substantially more concise than those that would involve enantiomerically pure substrates and achiral Mo alkylidenes or Ru-based carbenes. The scope of research towards design and development of chiral catalysts is not limited to discovery of complexes that are merely the chiral versions of the related achiral variants. A chiral olefin metathesis catalyst, in addition to furnishing products of high enantiomeric purity, can offer levels of efficiency, product selectivity and/or olefin stereoselectivity that are unavailable through the achiral variants. Such positive attributes of chiral catalysts (whether utilized in racemic or enantiomerically enriched form) should be considered as general, applicable to other classes of transformations.

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Year:  2010        PMID: 19967680      PMCID: PMC3517032          DOI: 10.1002/anie.200904491

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


  61 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.  Chiral Ru-based complexes for asymmetric olefin metathesis: enhancement of catalyst activity through steric and electronic modifications.

Authors:  Joshua J Van Veldhuizen; Dennis G Gillingham; Steven B Garber; Osamu Kataoka; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2003-10-15       Impact factor: 15.419

3.  Rate enhancement by ethylene in the Ru-catalyzed ring-closing metathesis of enynes: evidence for an "ene-then-yne" pathway that diverts through a second catalytic cycle.

Authors:  Guy C Lloyd-Jones; Robert G Margue; Johannes G de Vries
Journal:  Angew Chem Int Ed Engl       Date:  2005-12-01       Impact factor: 15.336

4.  Rhodium-catalyzed asymmetric addition of aryl- and alkenylboronic acids to isatins.

Authors:  Ryo Shintani; Mitsunori Inoue; Tamio Hayashi
Journal:  Angew Chem Int Ed Engl       Date:  2006-05-12       Impact factor: 15.336

Review 5.  The remarkable metal-catalysed olefin metathesis reaction.

Authors:  Amir H Hoveyda; Adil R Zhugralin
Journal:  Nature       Date:  2007-11-08       Impact factor: 49.962

6.  Understanding d(0)-olefin metathesis catalysts: which metal, which ligands?

Authors:  Albert Poater; Xavier Solans-Monfort; Eric Clot; Christophe Copéret; Odile Eisenstein
Journal:  J Am Chem Soc       Date:  2007-06-09       Impact factor: 15.419

7.  Total synthesis of (-)-tuberostemonine.

Authors:  Peter Wipf; Stacey R Rector; Hidenori Takahashi
Journal:  J Am Chem Soc       Date:  2002-12-18       Impact factor: 15.419

8.  Enantioselective synthesis of allylsilanes bearing tertiary and quaternary Si-substituted carbons through Cu-catalyzed allylic alkylations with alkylzinc and arylzinc reagents.

Authors:  Monica A Kacprzynski; Tricia L May; Stephanie A Kazane; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

9.  Enantioselective total synthesis of erogorgiaene: applications of asymmetric Cu-catalyzed conjugate additions of alkylzincs to acyclic enones.

Authors:  Richard R Cesati; Judith de Armas; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2004-01-14       Impact factor: 15.419

10.  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

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  26 in total

1.  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

2.  Synthesis of Linear (Z)-α,β-Unsaturated Esters by Catalytic Cross-Metathesis. The Influence of Acetonitrile.

Authors:  Elsie C Yu; Brett M Johnson; Erik M Townsend; Richard R Schrock; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

3.  Traceless Protection for More Broadly Applicable Olefin Metathesis.

Authors:  Yucheng Mu; Thach T Nguyen; Farid W van der Mei; Richard R Schrock; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-13       Impact factor: 15.336

4.  Synthesis of (±)-tetrapetalone A-Me aglycon.

Authors:  Peter N Carlsen; Tyler J Mann; Amir H Hoveyda; Alison J Frontier
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-07       Impact factor: 15.336

5.  Catalytic Z-selective cross-metathesis with secondary silyl- and benzyl-protected allylic ethers: mechanistic aspects and applications to natural product synthesis.

Authors:  Tyler J Mann; Alexander W H Speed; Richard R Schrock; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-21       Impact factor: 15.336

6.  Highly Z-selective and enantioselective ring-opening/cross-metathesis catalyzed by a resolved stereogenic-at-Ru complex.

Authors:  John Hartung; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2013-07-03       Impact factor: 15.419

7.  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

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

Authors:  John Hartung; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2014-02-19       Impact factor: 15.336

9.  Reactivation of a Ruthenium-Based Olefin Metathesis Catalyst.

Authors:  Daniel S Tabari; Daniel R Tolentino; Yann Schrodi
Journal:  Organometallics       Date:  2012-12-21       Impact factor: 3.876

10.  Efficient and selective formation of macrocyclic disubstituted Z alkenes by ring-closing metathesis (RCM) reactions catalyzed by Mo- or W-based monoaryloxide pyrrolide (MAP) complexes: applications to total syntheses of epilachnene, yuzu lactone, ambrettolide, epothilone C, and nakadomarin A.

Authors:  Chenbo Wang; Miao Yu; Andrew F Kyle; Pavol Jakubec; Darren J Dixon; Richard R Schrock; Amir H Hoveyda
Journal:  Chemistry       Date:  2013-01-23       Impact factor: 5.236

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