Literature DB >> 12059222

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.

Sarah J Dolman1, Elizabeth S Sattely, Amir H Hoveyda, Richard R Schrock.   

Abstract

The first catalytic asymmetric ring-closing metathesis method for the synthesis of N-containing heterocycles is reported; this is accomplished through Mo-catalyzed kinetic resolution or desymmetrization of unsaturated amines. Importantly, this catalytic asymmetric method delivers medium-ring unsaturated amines (including eight-membered rings) in high yield, with exceptional enantioselectivity and without the need for solvents. These enantioselective reactions can be effected by catalysts prepared in situ from commercially available reagents.

Entities:  

Mesh:

Substances:

Year:  2002        PMID: 12059222     DOI: 10.1021/ja012534l

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


  8 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.  A green chemistry approach to asymmetric catalysis: solvent-free and highly concentrated reactions.

Authors:  Patrick J Walsh; Hongmei Li; Cecilia Anaya de Parrodi
Journal:  Chem Rev       Date:  2007-05-27       Impact factor: 60.622

3.  Highly concentrated catalytic asymmetric allylation of ketones.

Authors:  Alfred J Wooten; Jeung Gon Kim; Patrick J Walsh
Journal:  Org Lett       Date:  2007-02-01       Impact factor: 6.005

4.  The mechanism and an improved asymmetric allylboration of ketones catalyzed by chiral biphenols.

Authors:  David S Barnett; Philip N Moquist; Scott E Schaus
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.  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

7.  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

8.  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

  8 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.