Literature DB >> 26273114

Construction of Tertiary Chiral Centers by Pd-catalyzed Asymmetric Allylic Alkylation of Prochiral Enolate Equivalents.

Yusuke Kita1, Yoshitaka Numajiri1, Noriko Okamoto1, Brian M Stoltz1.   

Abstract

The palladium-catalyzed decarboxylative allylic alkylation of enol carbonates derived from lactams and ketones is described. Employing these substrates with an electronically tuned Pd catalyst system trisubstituted chiral centers are produced. These stereocenters have been previously challenging to achieve using Pd complex/chiral P-N ligand systems.

Entities:  

Keywords:  alkylation; catalysis; enantioselective; palladium

Year:  2015        PMID： 26273114      PMCID： PMC4528676          DOI： 10.1016/j.tet.2015.05.092

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  24 in total

1.  A new approach to the synthesis of peptidomimetic renin inhibitors: palladium-catalyzed asymmetric allylation of acyclic alkyl aryl ketones.

Authors:  Stephen Hanessian; Etienne Chénard
Journal:  Org Lett       Date:  2012-06-05       Impact factor: 6.005

2.  Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.

Authors:  Barry M Trost; Matthew L Crawley
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

3.  The enantioselective Tsuji allylation.

Authors:  Douglas C Behenna; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2004-11-24       Impact factor: 15.419

4.  Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides.

Authors:  Nolan T McDougal; Jan Streuff; Herschel Mukherjee; Scott C Virgil; Brian M Stoltz
Journal:  Tetrahedron Lett       Date:  2010-10-20       Impact factor: 2.415

Review 5.  The economies of synthesis.

Authors:  Timothy Newhouse; Phil S Baran; Reinhard W Hoffmann
Journal:  Chem Soc Rev       Date:  2009-08-21       Impact factor: 54.564

6.  The catalytic enantioselective total synthesis of (+)-liphagal.

Authors:  Joshua J Day; Ryan M McFadden; Scott C Virgil; Helene Kolding; Jennifer L Alleva; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-10       Impact factor: 15.336

7.  Enantioselective synthesis of α-secondary and α-tertiary piperazin-2-ones and piperazines by catalytic asymmetric allylic alkylation.

Authors:  Katerina M Korch; Christian Eidamshaus; Douglas C Behenna; Sangkil Nam; David Horne; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-07       Impact factor: 15.336

Review 8.  Function-oriented synthesis, step economy, and drug design.

Authors:  Paul A Wender; Vishal A Verma; Thomas J Paxton; Thomas H Pillow
Journal:  Acc Chem Res       Date:  2007-12-27       Impact factor: 22.384

9.  PREPARATION OF (S)-tert-ButylPHOX (Oxazole, 4-(1,1-dimethylethyl)-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro- (4S)-).

Authors:  Michael R Krout; Justin T Mohr; Brian M Stoltz
Journal:  Organic Synth       Date:  2009-01-01

10.  Enantioselective synthesis of α-quaternary Mannich adducts by palladium-catalyzed allylic alkylation: total synthesis of (+)-sibirinine.

Authors:  Yoshitaka Numajiri; Beau P Pritchett; Koji Chiyoda; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2015-01-20       Impact factor: 15.419
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  1 in total

1.  Oxidation of Hindered Allylic C-H Bonds with Applications to the Functionalization of Complex Molecules.

Authors:  Zachary C Litman; Ankit Sharma; John F Hartwig
Journal:  ACS Catal       Date:  2017-01-30       Impact factor: 13.084
  1 in total

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