Literature DB >> 16381588

Enantioselective addition of terminal alkynes to isolated isoquinoline iminiums.

Alexander M Taylor1, Stuart L Schreiber.   

Abstract

[reaction: see text] The asymmetric, catalytic addition of terminal alkynes to discrete alkyliminium species in the presence of copper bromide, QUINAP ligand, and triethylamine is reported. The reaction proceeds in high yield and high enantiomeric excess with a variety of substrates in solution and is also amenable to solid-phase synthesis.

Entities:  

Year:  2006        PMID： 16381588     DOI： 10.1021/ol0526165

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


  11 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

2.  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

3.  Enantioselective and Diastereodivergent Allylation of Propargylic C-H Bonds.

Authors:  Jin Zhu; Yidong Wang; Aaron D Charlack; Yi-Ming Wang
Journal:  J Am Chem Soc       Date:  2022-08-17       Impact factor: 16.383

4.  Identification and characterization of novel sirtuin inhibitor scaffolds.

Authors:  Brandi D Sanders; Brittany Jackson; Michael Brent; Alexander M Taylor; Weiwei Dang; Shelley L Berger; Stuart L Schreiber; Konrad Howitz; Ronen Marmorstein
Journal:  Bioorg Med Chem       Date:  2009-08-03       Impact factor: 3.641

5.  Identification of novel epoxide inhibitors of hepatitis C virus replication using a high-throughput screen.

Authors:  Lee F Peng; Sun Suk Kim; Sirinya Matchacheep; Xiaoguang Lei; Shun Su; Wenyu Lin; Weerawat Runguphan; Won-Hyeok Choe; Naoya Sakamoto; Masanori Ikeda; Nobuyuki Kato; Aaron B Beeler; John A Porco; Stuart L Schreiber; Raymond T Chung
Journal:  Antimicrob Agents Chemother       Date:  2007-08-06       Impact factor: 5.191

6.  Enantioselective, Copper-Catalyzed Alkynylation of Ketimines To Deliver Isoquinolines with α-Diaryl Tetrasubstituted Stereocenters.

Authors:  Srimoyee Dasgupta; Jixin Liu; Clarissa A Shoffler; Glenn P A Yap; Mary P Watson
Journal:  Org Lett       Date:  2016-11-16       Impact factor: 6.005

7.  Synthesis of 8-phenyl substituted 3-benzazecines with allene moiety, their thermal rearrangement and evaluation as acetylcholinesterase inhibitors.

Authors:  Maxim S Kobzev; Alexander A Titov; Elena V Alexandrova; Rosa Purgatorio; Marco Catto; Elena A Sorokina; Tatiana N Borisova; Alexey V Varlamov; Cosimo D Altomare; Leonid G Voskressensky
Journal:  Mol Divers       Date:  2021-02-04       Impact factor: 2.943

8.  Biocatalytic organic synthesis of optically pure (S)-scoulerine and berbine and benzylisoquinoline alkaloids.

Authors:  Joerg H Schrittwieser; Verena Resch; Silvia Wallner; Wolf-Dieter Lienhart; Johann H Sattler; Jasmin Resch; Peter Macheroux; Wolfgang Kroutil
Journal:  J Org Chem       Date:  2011-07-19       Impact factor: 4.354

9.  Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives.

Authors:  Alejandro A Orden; Joerg H Schrittwieser; Verena Resch; Francesco G Mutti; Wolfgang Kroutil
Journal:  Tetrahedron Asymmetry       Date:  2013-06-30

Review 10.  Enantioselective additions of copper acetylides to cyclic iminium and oxocarbenium ions.

Authors:  Jixin Liu; Srimoyee Dasgupta; Mary P Watson
Journal:  Beilstein J Org Chem       Date:  2015-12-22       Impact factor: 2.883
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