Literature DB >> 15228272

Synthesis and reactivity of mixed alkynylalanes by direct triethylamine-catalyzed alumination of terminal alkynes.

Christophe Feuvrie1, Jérôme Blanchet, Martine Bonin, Laurent Micouin.   

Abstract

[reaction: see text] Terminal alumination of alkynes by DIBALH or trimethylaluminum can be performed in a simple manner in the presence of a small amount of triethylamine. This new Lewis-base-catalyzed process delivers mixed alkynyldialkylalanes of great interest, without the need of an initial deprotonation step with lithium or sodium derivatives followed by a transmetalation.

Entities:  

Year:  2004        PMID: 15228272     DOI: 10.1021/ol049346v

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


  4 in total

1.  Gold(I)-Catalyzed Hydration of Allenes.

Authors:  Zhibin Zhang; Seong Du Lee; Aaron S Fisher; Ross A Widenhoefer
Journal:  Tetrahedron       Date:  2009-02-28       Impact factor: 2.457

2.  Enantioselective synthesis of alkyne-substituted quaternary carbon stereogenic centers through NHC-Cu-catalyzed allylic substitution reactions with (i-Bu)2(alkynyl)aluminum reagents.

Authors:  Jennifer A Dabrowski; Fang Gao; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2011-03-08       Impact factor: 15.419

3.  Combining NHC-Cu and Brønsted base catalysis: enantioselective allylic substitution/conjugate additions with alkynylaluminum reagents and stereospecific isomerization of the products to trisubstituted allenes.

Authors:  Jennifer A Dabrowski; Fredrik Haeffner; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-18       Impact factor: 15.336

4.  Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics.

Authors:  Matthias Wünsch; David Schröder; Tanja Fröhr; Lisa Teichmann; Sebastian Hedwig; Nils Janson; Clara Belu; Jasmin Simon; Shari Heidemeyer; Philipp Holtkamp; Jens Rudlof; Lennard Klemme; Alessa Hinzmann; Beate Neumann; Hans-Georg Stammler; Norbert Sewald
Journal:  Beilstein J Org Chem       Date:  2017-11-15       Impact factor: 2.883

  4 in total

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