Literature DB >> 25580807

Enantioselective rhodium-catalyzed isomerization of 4-iminocrotonates: asymmetric synthesis of a unique chiral synthon.

Wen-Zhen Zhang1, John C K Chu, Kevin M Oberg, Tomislav Rovis.   

Abstract

An enantioselective isomerization of 4-iminocrotonates catalyzed by a rhodium(I)/phosphoramidite complex is described. This reaction uses widely available amines to couple with 4-oxocrotonate to provide a convenient access to a central chiral building block in good yield and high enantioselectivity. Although the mechanism of this new transformation remains unclear, both Rh and the phosphoramidite play a central role.

Entities:  

Mesh：

Substances：

Year:  2015        PMID： 25580807      PMCID： PMC4986700          DOI： 10.1021/ja510348p

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


  26 in total

1.  Enantioselective Pictet-Spengler-type cyclizations of hydroxylactams: H-bond donor catalysis by anion binding.

Authors:  Izzat T Raheem; Parvinder S Thiara; Emily A Peterson; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2007-10-17       Impact factor: 15.419

2.  Asymmetric spiroacetalization catalysed by confined Brønsted acids.

Authors:  Ilija Čorić; Benjamin List
Journal:  Nature       Date:  2012-03-14       Impact factor: 49.962

3.  Rhodium-catalyzed [2 + 2 + 2] cycloaddition of alkenyl isocyanates and alkynes.

Authors:  Robert T Yu; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2006-03-08       Impact factor: 15.419

4.  N-Acyliminium ion chemistry: highly efficient and versatile carbon-carbon bond formation by nucleophilic substitution of hydroxy groups catalyzed by Sn(NTf(2))(4).

Authors:  Raja Ben Othman; Radouane Affani; Marie-José Tranchant; Sylvain Antoniotti; Vincent Dalla; Elisabet Duñach
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

5.  Enantioselective rhodium-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and terminal alkynes: application to the total synthesis of (+)-lasubine II.

Authors:  Robert T Yu; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2006-09-27       Impact factor: 15.419

6.  Enantioselective Synthesis of the Tricyclic Core of FR901483 Featuring a Rh-Catalyzed [2+2+2] Cycloaddition.

Authors:  Stéphane Perreault; Tomislav Rovis
Journal:  Synthesis (Stuttg)       Date:  2013       Impact factor: 3.157

7.  Enantioselective Brønsted acid-catalyzed N-acyliminium cyclization cascades.

Authors:  Michael E Muratore; Chloe A Holloway; Adam W Pilling; R Ian Storer; Graham Trevitt; Darren J Dixon
Journal:  J Am Chem Soc       Date:  2009-08-12       Impact factor: 15.419

8.  Total synthesis of indolizidine alkaloid (-)-209D: overriding substrate bias in the asymmetric rhodium-catalyzed [2+2+2] cycloaddition.

Authors:  Robert T Yu; Ernest E Lee; Guillaume Malik; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Enantioselective synthesis of the R-enantiomer of the feeding deterrent (S)-ypaoamide.

Authors:  Jie Chen; Pei-Qiang Huang; Yves Queneau
Journal:  J Org Chem       Date:  2009-10-02       Impact factor: 4.354

10.  Design, synthesis, and structure-activity relationship studies of new phenolic DNA gyrase inhibitors.

Authors:  Thomas Lübbers; Peter Angehrn; Hans Gmünder; Silvia Herzig
Journal:  Bioorg Med Chem Lett       Date:  2006-12-22       Impact factor: 2.823
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.