Literature DB >> 15056762

Mo-catalyzed asymmetric olefin metathesis in target-oriented synthesis: enantioselective synthesis of (+)-africanol.

Gabriel S Weatherhead1, G A Cortez, Richard R Schrock, Amir H Hoveyda.   

Abstract

Catalytic asymmetric ring-opening metathesis (AROM) provides an efficient method for the synthesis of a variety of optically enriched small organic molecules that cannot be easily prepared by alternative methods. The development of Mo-catalyzed AROM transformations that occur in tandem with ring-closing metathesis are described. The utility of the Mo-catalyzed AROM/ring-closing metathesis is demonstrated through an enantioselective approach to the synthesis of (+)-africanol.

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Year:  2004        PMID: 15056762      PMCID: PMC395989          DOI: 10.1073/pnas.0307589101

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN: 0027-8424            Impact factor:   11.205


  12 in total

1.  An enantiomerically pure adamantylimido molybdenum alkylidene complex. An effective new catalyst for enantioselective olefin metathesis.

Authors:  W C Peter Tsang; Jesper A Jernelius; G A Cortez; Gabriel S Weatherhead; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2003-03-05       Impact factor: 15.419

2.  Synthetic and mechanistic studies of the retro-Claisen rearrangement. 4. An application to the total synthesis of (+)-Laurenyne.

Authors:  Robert K Boeckman; Jing Zhang; Michael R Reeder
Journal:  Org Lett       Date:  2002-10-31       Impact factor: 6.005

3.  Development of bifunctional salen catalysts: rapid, chemoselective alkylations of alpha-ketoesters.

Authors:  Erin F DiMauro; Marisa C Kozlowski
Journal:  J Am Chem Soc       Date:  2002-10-30       Impact factor: 15.419

4.  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

5.  Catalytic asymmetric ring-opening metathesis/cross metathesis (AROM/CM) reactions. Mechanism and application to enantioselective synthesis of functionalized cyclopentanes.

Authors:  D S La; E S Sattely; J G Ford; R R Schrock; A H Hoveyda
Journal:  J Am Chem Soc       Date:  2001-08-15       Impact factor: 15.419

6.  Enantioselective ruthenium-catalyzed ring-closing metathesis.

Authors:  T J Seiders; D W Ward; R H Grubbs
Journal:  Org Lett       Date:  2001-10-04       Impact factor: 6.005

7.  Enantioselective synthesis of medium-ring heterocycles, tertiary ethers, and tertiary alcohols by Mo-catalyzed ring-closing metathesis.

Authors:  Andrew F Kiely; Jesper A Jernelius; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2002-03-27       Impact factor: 15.419

8.  Enhancement of enantioselectivity by THF in asymmetric mo-catalyzed olefin metathesis. Catalytic enantioselective synthesis of cyclic tertiary ethers and spirocycles.

Authors:  Xin Teng; Dustin R Cefalo; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2002-09-11       Impact factor: 15.419

9.  Enantioselective synthesis of cyclic secondary amines through Mo-catalyzed asymmetric ring-closing metathesis (ARCM).

Authors:  Sarah J Dolman; Richard R Schrock; Amir H Hoveyda
Journal:  Org Lett       Date:  2003-12-11       Impact factor: 6.005

10.  Efficient catalytic enantioselective synthesis of unsaturated amines: preparation of small- and medium-ring cyclic amines through mo-catalyzed asymmetric ring-closing metathesis in the absence of solvent.

Authors:  Sarah J Dolman; Elizabeth S Sattely; Amir H Hoveyda; Richard R Schrock
Journal:  J Am Chem Soc       Date:  2002-06-19       Impact factor: 15.419

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  8 in total

1.  Synthesis of the reported structure of trans-africanan-1α-ol.

Authors:  Douglass F Taber; Sha Bai; Weiwei Tian
Journal:  J Org Chem       Date:  2011-11-10       Impact factor: 4.354

Review 2.  Catalytic enantioselective olefin metathesis in natural product synthesis. Chiral metal-based complexes that deliver high enantioselectivity and more.

Authors:  Amir H Hoveyda; Steven J Malcolmson; Simon J Meek; Adil R Zhugralin
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

3.  Endo-selective enyne ring-closing metathesis promoted by stereogenic-at-Mo monoalkoxide and monoaryloxide complexes. Efficient synthesis of cyclic dienes not accessible through reactions with Ru carbenes.

Authors:  Yeon-Ju Lee; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-08-05       Impact factor: 15.419

4.  Design and stereoselective preparation of a new class of chiral olefin metathesis catalysts and application to enantioselective synthesis of quebrachamine: catalyst development inspired by natural product synthesis.

Authors:  Elizabeth S Sattely; Simon J Meek; Steven J Malcolmson; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-01-28       Impact factor: 15.419

5.  Asymmetric synthesis of medium-sized rings by intramolecular Au(I)-catalyzed cyclopropanation.

Authors:  Iain D G Watson; Stefanie Ritter; F Dean Toste
Journal:  J Am Chem Soc       Date:  2009-02-18       Impact factor: 15.419

6.  Stereoselectivity of supported alkene metathesis catalysts: a goal and a tool to characterize active sites.

Authors:  Christophe Copéret
Journal:  Beilstein J Org Chem       Date:  2011-01-05       Impact factor: 2.883

7.  Synthesis of amorpha-4,11-diene from dihydroartemisinic acid.

Authors:  Geoffrey Schwertz; Andrea Zanetti; Marllon Nascimento de Oliveira; Mario Andrès Gomez Fernandez; Fabienne Dioury; Janine Cossy; Zacharias Amara
Journal:  Tetrahedron       Date:  2019-02-08       Impact factor: 2.457

8.  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 in total

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