Literature DB >> 17536810

A facile and modular synthesis of phosphinooxazoline ligands.

Kousuke Tani1, Douglas C Behenna, Ryan M McFadden, Brian M Stoltz.   

Abstract

The copper(I) iodide catalyzed phosphine/aryl halide coupling procedure of Buchwald et al. provides modular, robust, and scaleable access to phosphinooxazoline (PHOX) ligands. The advantages of this method are highlighted by the convenient synthesis of PHOX ligands with varied steric and electronic properties, which would be challenging to synthesize by other protocols.

Entities:  

Year:  2007        PMID： 17536810     DOI： 10.1021/ol070884s

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


  31 in total

1.  A catalytic, asymmetric formal synthesis of (+)-hamigeran B.

Authors:  Herschel Mukherjee; Nolan T McDougal; Scott C Virgil; Brian M Stoltz
Journal:  Org Lett       Date:  2011-01-27       Impact factor: 6.005

2.  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

3.  High-Throughput Screening of the Asymmetric Decarboxylative Alkylation Reaction of Enolate-Stabilized Enol Carbonates.

Authors:  Nolan T McDougal; Scott C Virgil; Brian M Stoltz
Journal:  Synlett       Date:  2010-01-01       Impact factor: 2.454

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

Authors:  Yusuke Kita; Yoshitaka Numajiri; Noriko Okamoto; Brian M Stoltz
Journal:  Tetrahedron       Date:  2015-09-16       Impact factor: 2.457

5.  The catalytic asymmetric total synthesis of elatol.

Authors:  David E White; Ian C Stewart; Robert H Grubbs; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2007-12-29       Impact factor: 15.419

6.  Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors:  Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal:  Chem Rev       Date:  2021-05-21       Impact factor: 60.622

7.  Model Studies To Access the [6,7,5,5]-Core of Ineleganolide Using Tandem Translactonization-Cope or Cyclopropanation-Cope Rearrangements as Key Steps.

Authors:  Jennifer L Roizen; Amanda C Jones; Russell C Smith; Scott C Virgil; Brian M Stoltz
Journal:  J Org Chem       Date:  2017-11-21       Impact factor: 4.354

8.  Expanding insight into asymmetric palladium-catalyzed allylic alkylation of N-heterocyclic molecules and cyclic ketones.

Authors:  Nathan B Bennett; Douglas C Duquette; Jimin Kim; Wen-Bo Liu; Alexander N Marziale; Douglas C Behenna; Scott C Virgil; Brian M Stoltz
Journal:  Chemistry       Date:  2013-02-27       Impact factor: 5.236

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.  Synthesis and Exploration of Electronically Modified (R)-5,5-Dimethyl-(p-CF3)3-i-PrPHOX in Palladium-Catalyzed Enantio- and Diastereoselective Allylic Alkylation: A Practical Alternative to (R)-(p-CF3)3-t-BuPHOX.

Authors:  Robert A Craig; Brian M Stoltz
Journal:  Tetrahedron Lett       Date:  2015-08-05       Impact factor: 2.415
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