Literature DB >> 11902866

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

Andrew F Kiely1, Jesper A Jernelius, Richard R Schrock, Amir H Hoveyda.   

Abstract

The Mo-catalyzed asymmetric ring-closing metathesis (ARCM) of various achiral trienes leads to the formation of medium-ring unsaturated heterocycles in high yield and with excellent enantioselectivity. Reactions may be carried out on gram scale and in the absence of solvent. The unsaturated siloxanes obtained enantioselectively can be readily functionalized to obtain synthetically useful and difficult-to-access tertiary alcohols.

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Year:  2002        PMID: 11902866     DOI: 10.1021/ja012679s

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


  11 in total

1.  Diastereoselective temporary silicon-tethered ring-closing-metathesis reactions with prochiral alcohols: a new approach to long-range asymmetric induction.

Authors:  P Andrew Evans; Jian Cui; Gerald P Buffone
Journal:  Angew Chem Int Ed Engl       Date:  2003-04-17       Impact factor: 15.336

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

Authors:  Gabriel S Weatherhead; G A Cortez; Richard R Schrock; Amir H Hoveyda
Journal:  Proc Natl Acad Sci U S A       Date:  2004-03-31       Impact factor: 11.205

3.  Recent advances in the application of ring-closing metathesis for the synthesis of unsaturated nitrogen heterocycles.

Authors:  Emilia J Groso; Corinna S Schindler
Journal:  Synthesis (Stuttg)       Date:  2019-02-08       Impact factor: 3.157

4.  Enantioselective synthesis of P-stereogenic phosphinates and phosphine oxides by molybdenum-catalyzed asymmetric ring-closing metathesis.

Authors:  James Stephen Harvey; Steven J Malcolmson; Katherine S Dunne; Simon J Meek; Amber L Thompson; Richard R Schrock; Amir H Hoveyda; Véronique Gouverneur
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

5.  Highly efficient molybdenum-based catalysts for enantioselective alkene metathesis.

Authors:  Steven J Malcolmson; Simon J Meek; Elizabeth S Sattely; Richard R Schrock; Amir H Hoveyda
Journal:  Nature       Date:  2008-11-16       Impact factor: 49.962

6.  Mechanism of NHC-Catalyzed Conjugate Additions of Diboron and Borosilane Reagents to α,β-Unsaturated Carbonyl Compounds.

Authors:  Hao Wu; Jeannette M Garcia; Fredrik Haeffner; Suttipol Radomkit; Adil R Zhugralin; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2015-08-11       Impact factor: 15.419

7.  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

8.  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

9.  NHC-Cu-Catalyzed Silyl Conjugate Additions to Acyclic and Cyclic Dienones and Dienoates. Efficient Site-, Diastereo- and Enantioselective Synthesis of Carbonyl-Containing Allylsilanes.

Authors:  Kang-Sang Lee; Hao Wu; Fredrik Haeffner; Amir H Hoveyda
Journal:  Organometallics       Date:  2012-09-19       Impact factor: 3.876

10.  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

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