Literature DB >> 19226124

Selective vinyl C-H lithiation of cis-stilbenes.

Thomas Tricotet1, Patricia Fleming, Juliet Cotter, Anne-Marie L Hogan, Carsten Strohmann, Viktoria H Gessner, Donal F O'Shea.   

Abstract

A stereochemistry-controlled suppression of carbolithiation facilitated a regioselective vinyl C-H lithiation of cis-stilbenes allowing routine regio- and stereoselective access to polysubstituted alkenes and heterocycles. This unique selectivity was obtained for numerous directing groups and could be rationalized with DFT computational studies and an experimental mechanistic illustration of a unique anion migration.

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Year:  2009        PMID: 19226124     DOI: 10.1021/ja809941n

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  4 in total

1.  One-pot two-step synthesis of 3-iodo-4-aryloxy coumarins and their Pd/C-catalyzed annulation to coumestans.

Authors:  Niranjan Panda; Irshad Mattan
Journal:  RSC Adv       Date:  2018-02-16       Impact factor: 4.036

2.  Use of mixed Li/K metal TMP amide (LiNK chemistry) for the synthesis of [2.2]metacyclophanes.

Authors:  Marco Blangetti; Patricia Fleming; Donal F O'Shea
Journal:  Beilstein J Org Chem       Date:  2011-09-09       Impact factor: 2.883

3.  Developing a hetero-alkali-metal chemistry of 2,2,6,6-tetramethylpiperidide (TMP): stoichiometric and structural diversity within a series of lithium/sodium, lithium/potassium and sodium/potassium TMP compounds.

Authors:  David R Armstrong; Alan R Kennedy; Robert E Mulvey; Stuart D Robertson
Journal:  Chemistry       Date:  2011-07-15       Impact factor: 5.236

4.  Crystal structure and Hirshfeld surface analysis of N-{[diphen-yl(vin-yl)sil-yl]meth-yl}-2-methyl-propan-2-ammonium chloride.

Authors:  Christoph Schwab; Andreas Voss; Carsten Strohmann
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2022-09-22
  4 in total

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