Literature DB >> 21995597

Enantioselective syntheses of (+)-sertraline and (+)-indatraline using lithiation/borylation-protodeboronation methodology.

Stefan Roesner1, Javier Mansilla Casatejada, Tim G Elford, Ravindra P Sonawane, Varinder K Aggarwal.   

Abstract

The lithiation/borylation-protodeboronation of a homoallyl carbamate was applied to the synthesis of (+)-sertraline and (+)-indatraline. Due to the presence of the alkene, significant modifications of the methodology were required (use of 12-crown-4, TMSCl, H(2)O), or a solvent switch to CHCl(3), to achieve high yields and high selectivities.
© 2011 American Chemical Society

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Year:  2011        PMID： 21995597     DOI： 10.1021/ol202251p

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


  14 in total

1.  A General, Simple Catalyst for Enantiospecific Cross Couplings of Benzylic Ammonium Triflates and Boronic Acids: No Phosphine Ligand Required.

Authors:  Danielle M Shacklady-McAtee; Kelsey M Roberts; Corey H Basch; Ye-Geun Song; Mary P Watson
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

2.  Synthesis of hydroxyphthioceranic acid using a traceless lithiation-borylation-protodeboronation strategy.

Authors:  Ramesh Rasappan; Varinder K Aggarwal
Journal:  Nat Chem       Date:  2014-07-27       Impact factor: 24.427

3.  Nickel-catalyzed cross-couplings of benzylic pivalates with arylboroxines: stereospecific formation of diarylalkanes and triarylmethanes.

Authors:  Qi Zhou; Harathi D Srinivas; Srimoyee Dasgupta; Mary P Watson
Journal:  J Am Chem Soc       Date:  2013-02-20       Impact factor: 15.419

4.  Asymmetric synthesis via stereospecific C-N and C-O bond activation of alkyl amine and alcohol derivatives.

Authors:  Sarah M Pound; Mary P Watson
Journal:  Chem Commun (Camb)       Date:  2018-10-30       Impact factor: 6.222

5.  Promoter free allylation of trichloroacetimidates with allyltributylstannanes under thermal conditions to access the common 1,1'-diarylbutyl pharmacophore.

Authors:  Nivedita S Mahajani; John D Chisholm
Journal:  Org Biomol Chem       Date:  2018-05-30       Impact factor: 3.876

6.  Nickel-catalyzed cross couplings of benzylic ammonium salts and boronic acids: stereospecific formation of diarylethanes via C-N bond activation.

Authors:  Prantik Maity; Danielle M Shacklady-McAtee; Glenn P A Yap; Eric R Sirianni; Mary P Watson
Journal:  J Am Chem Soc       Date:  2012-12-26       Impact factor: 15.419

7.  Enantioselective synthesis of (R)-tolterodine using lithiation/borylation-protodeboronation methodology.

Authors:  Stefan Roesner; Varinder K Aggarwal
Journal:  Can J Chem       Date:  2012-11       Impact factor: 1.118

8.  Iridium-Catalyzed Enantioselective Allylic Substitution of Enol Silanes from Vinylogous Esters and Amides.

Authors:  Ming Chen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-10-23       Impact factor: 15.419

9.  Nickel-Catalyzed Borylation of Benzylic Ammonium Salts: Stereospecific Synthesis of Enantioenriched Benzylic Boronates.

Authors:  Corey H Basch; Kelsey M Cobb; Mary P Watson
Journal:  Org Lett       Date:  2015-12-17       Impact factor: 6.005

10.  Enantioselective and Regiodivergent Copper-Catalyzed Electrophilic Arylation of Allylic Amides with Diaryliodonium Salts.

Authors:  Elise Cahard; Henry P J Male; Matthieu Tissot; Matthew J Gaunt
Journal:  J Am Chem Soc       Date:  2015-06-19       Impact factor: 15.419
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