Literature DB >> 14653702

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

Sarah J Dolman1, Richard R Schrock, Amir H Hoveyda.   

Abstract

Carbocyclic amines are synthesized efficiently in up to 93% ee by asymmetric ring-closing metathesis (ARCM) with 2-5 mol % chiral Mo complexes. An example is provided where the catalyst is prepared in situ (catalyst isolation not needed) to afford secondary amines that cannot be prepared by alternative methods. [reaction: see text]

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Year:  2003        PMID: 14653702     DOI: 10.1021/ol036026n

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  11 in total

1.  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

2.  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

3.  Novel approach to the lundurine alkaloids: synthesis of the tetracyclic core.

Authors:  Suvi T M Orr; Jianhua Tian; Meike Niggemann; Stephen F Martin
Journal:  Org Lett       Date:  2011-09-02       Impact factor: 6.005

4.  3-Boryl-2,1-borazaronaphthalene: Umpolung Reagents for Diversifying Naphthalene Isosteres.

Authors:  Jordan S Compton; Borna Saeednia; Christopher B Kelly; Gary A Molander
Journal:  J Org Chem       Date:  2018-07-10       Impact factor: 4.354

5.  A convergent, modular approach to functionalized 2,1-borazaronaphthalenes from 2-aminostyrenes and potassium organotrifluoroborates.

Authors:  Steven R Wisniewski; Courtney L Guenther; O Andreea Argintaru; Gary A Molander
Journal:  J Org Chem       Date:  2013-12-11       Impact factor: 4.354

6.  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

7.  Synthesis of phosphaformamidines and phosphaformamidinates.

Authors:  Maoying Song; Bruno Donnadieu; Michele Soleilhavoup; Guy Bertrand
Journal:  Chem Asian J       Date:  2007-07-02

8.  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

9.  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

10.  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

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