Literature DB >> 23734611

Development of asymmetric deacylative allylation.

Alexander J Grenning1, Christie K Van Allen, Tapan Maji, Simon B Lang, Jon A Tunge.   

Abstract

Herein we present the development of asymmetric deacylative allylation of ketone enolates. The reaction directly couples readily available ketone pronucleophiles with allylic alcohols using facile retro-Claisen cleavage to form reactive intermediates in situ. The simplicity and robustness of the reaction conditions is demonstrated by the preparation of >6 g of an allylated tetralone from commercially available materials. Furthermore, use of nonracemic PHOX ligands allows intermolecular formation of quaternary stereocenters directly from allylic alcohols.

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Year:  2013        PMID: 23734611      PMCID: PMC3827786          DOI: 10.1021/jo400793a

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  35 in total

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5.  Tandem palladium(0) and palladium(II)-catalyzed allylic alkylation through complementary redox cycles.

Authors:  Barry M Trost; David A Thaisrivongs; Max M Hansmann
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7.  Diastereoselective palladium-catalyzed formate reduction of allylic carbonates en route to polypropionate systems.

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Journal:  J Org Chem       Date:  2006-03-03       Impact factor: 4.354

8.  Mechanistic insights on the cycloisomerization of polyunsaturated precursors catalyzed by platinum and gold complexes.

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Authors:  Gilles Lemière; Bastien Cacciuttolo; Emilie Belhassen; Elisabet Duñach
Journal:  Org Lett       Date:  2012-05-11       Impact factor: 6.005

10.  Palladium-catalyzed synthesis and isolation of functionalized allylboronic acids: selective, direct allylboration of ketones.

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  3 in total

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2.  Development of (trimethylsilyl)ethyl ester protected enolates and applications in palladium-catalyzed enantioselective allylic alkylation: intermolecular cross-coupling of functionalized electrophiles.

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Review 3.  The Allylic Alkylation of Ketone Enolates.

Authors:  Lukas Junk; Uli Kazmaier
Journal:  ChemistryOpen       Date:  2020-09-10       Impact factor: 2.630

  3 in total

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