Literature DB >> 16562922

Diastereospecific intramolecular Ullmann couplings: unique chiral auxiliary for the preparation of 3,3'-disubstituted MeO-BIPHEP derivatives.

E Gorobets1, R McDonald, B A Keay.   

Abstract

[reaction: see text] A chiral auxiliary is described that provides only one diastereomer during intramolecular Ullmann couplings. Treatment of five Ullmann coupling precursors with Cu powder in DMF at 115 degrees C provides 2,2',3,3',6,6'-hexasubstituted 1,1'-biphenyls as single diastereomers in yields ranging from 66% to 91%.

Entities:  

Year:  2006        PMID: 16562922     DOI: 10.1021/ol060484p

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


  2 in total

1.  Synthesis of Axially Chiral 2,2'-Bisphosphobiarenes via a Nickel-Catalyzed Asymmetric Ullmann Coupling: General Access to Privileged Chiral Ligands without Optical Resolution.

Authors:  Ziqing Zuo; Raphael S Kim; Donald A Watson
Journal:  J Am Chem Soc       Date:  2021-01-13       Impact factor: 15.419

Review 2.  Recent advances in copper-catalyzed asymmetric coupling reactions.

Authors:  Fengtao Zhou; Qian Cai
Journal:  Beilstein J Org Chem       Date:  2015-12-15       Impact factor: 2.883

  2 in total

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