Literature DB >> 12123387

Efficient enantioselective additions of terminal alkynes and aldehydes under operationally convenient conditions.

Dean Boyall1, Doug E Frantz, Erick M Carreira.   

Abstract

[reaction: see text] The enantioselective addition reaction of terminal acetylenes and aldehydes mediated by Zn(OTf)2 and N-methyl ephedrine can be conducted with reagent grade solvent containing 84-1000 ppm H2O. The products can be isolated in high yield and useful enantioselectivities (up to 99% ee).

Entities:  

Year:  2002        PMID： 12123387     DOI： 10.1021/ol026282k

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


  26 in total

1.  Enantioselective copper-catalyzed alkynylation of benzopyranyl oxocarbenium ions.

Authors:  Harathi D Srinivas; Prantik Maity; Glenn P A Yap; Mary P Watson
Journal:  J Org Chem       Date:  2015-04-07       Impact factor: 4.354

Review 2.  Synthetic Strategies Employed for the Construction of Fostriecin and Related Natural Products.

Authors:  Barry M Trost; Joshua D Knopf; Cheyenne S Brindle
Journal:  Chem Rev       Date:  2016-12-08       Impact factor: 60.622

3.  Copper-catalyzed enantioselective additions to oxocarbenium ions: alkynylation of isochroman acetals.

Authors:  Prantik Maity; Harathi D Srinivas; Mary P Watson
Journal:  J Am Chem Soc       Date:  2011-10-11       Impact factor: 15.419

4.  An alkyne hydrosilylation-oxidation strategy for the selective installation of oxygen functionality.

Authors:  Barry M Trost; Zachary T Ball; Kai M Laemmerhold
Journal:  J Am Chem Soc       Date:  2005-07-20       Impact factor: 15.419

5.  Controlling Enantioselectivity in Additions to Cyclic Oxocarbenium Ions via Transition Metal Catalysis.

Authors:  Mary P Watson; Prantik Maity
Journal:  Synlett       Date:  2012       Impact factor: 2.454

6.  Chromium(0)-promoted [6pi + 2pi] cycloadditions of allenes with cycloheptatriene.

Authors:  James H Rigby; Stéphane B Laurent; Zeeshan Kamal; Mary Jane Heeg
Journal:  Org Lett       Date:  2008-12-18       Impact factor: 6.005

7.  Tunable Phosphoramidite Ligands for Asymmetric Hydrovinylation: Ligands par excellence for Generation of All-Carbon Quaternary Centers.

Authors:  Craig R Smith; Hwan Jung Lim; Aibin Zhang; T V Rajanbabu
Journal:  Synthesis (Stuttg)       Date:  2009-01-01       Impact factor: 3.157

8.  Spirodiepoxides: synthesis of epoxomicinoids.

Authors:  Yue Zhang; Joseph R Cusick; Partha Ghosh; Ning Shangguan; Sreenivas Katukojvala; Jennifer Inghrim; Thomas J Emge; Lawrence J Williams
Journal:  J Org Chem       Date:  2009-10-16       Impact factor: 4.354

9.  1,1'-Binaphthyl Ligands with Bulky 3,3'-Tertiaryalkyl Substituents for the Asymmetric Alkyne Addition to Aromatic Aldehydes.

Authors:  Qin Wang; Shan-Yong Chen; Xiao-Qi Yu; Lin Pu
Journal:  Tetrahedron       Date:  2007-05-21       Impact factor: 2.457

10.  All kinds of reactivity: recent breakthroughs in metal-catalyzed alkyne chemistry.

Authors:  Cecilia Anaya de Parrodi; Patrick J Walsh
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
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