Literature DB >> 15496112

Asymmetric allylic alkylation of ketone enolates: an asymmetric Claisen surrogate.

Erin C Burger1, Jon A Tunge.   

Abstract

[reaction: see text] The combination of catalytic palladium(0) and Trost ligand provides an effective catalyst for the rearrangement of allyl beta-ketoesters. The mechanism of the transformation involves formation of pi-allyl palladium intermediates which undergo enantioselective attack by ketone enolates. Decarboxylation of beta-ketocarboxylates allows regiospecific generation of enolates under extremely mild conditions.

Entities:  

Year:  2004        PMID： 15496112     DOI： 10.1021/ol048149t

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


  20 in total

1.  Mechanistic origin of the stereodivergence in decarboxylative allylation.

Authors:  Kalicharan Chattopadhyay; Ranjan Jana; Victor W Day; Justin T Douglas; Jon A Tunge
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

Review 2.  Transition metal-catalyzed decarboxylative allylation and benzylation reactions.

Authors:  Jimmie D Weaver; Antonio Recio; Alexander J Grenning; Jon A Tunge
Journal:  Chem Rev       Date:  2011-01-14       Impact factor: 60.622

3.  Iridium-Catalyzed Enantioselective Allylic Substitution of Aliphatic Esters with Silyl Ketene Acetals as the Ester Enolates.

Authors:  Xingyu Jiang; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-27       Impact factor: 15.336

4.  Decarboxylative benzylations of alkynes and ketones.

Authors:  Robert R P Torregrosa; Yamuna Ariyarathna; Kalicharan Chattopadhyay; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2010-07-14       Impact factor: 15.419

5.  Palladium-catalyzed decarboxylative sp3-sp3 coupling of nitrobenzene acetic esters.

Authors:  Shelli R Waetzig; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2007-11-08       Impact factor: 15.419

6.  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

7.  Decarboxylative allylation using sulfones as surrogates of alkanes.

Authors:  Jimmie D Weaver; Jon A Tunge
Journal:  Org Lett       Date:  2008-09-12       Impact factor: 6.005

8.  Palladium-catalyzed decarboxylative rearrangements of allyl 2,2,2-trifluoroethyl malonates: direct access to homoallylic esters.

Authors:  Lawrence P Tardibono; Jerod Patzner; Cara Cesario; Marvin J Miller
Journal:  Org Lett       Date:  2009-09-17       Impact factor: 6.005

9.  Palladium-catalyzed decarboxylative asymmetric allylic alkylation of enol carbonates.

Authors:  Barry M Trost; Jiayi Xu; Thomas Schmidt
Journal:  J Am Chem Soc       Date:  2009-12-30       Impact factor: 15.419

10.  Raising the pKa limit of "soft" nucleophiles in palladium-catalyzed allylic substitutions: application of diarylmethane pronucleophiles.

Authors:  Sheng-Chun Sha; Jiadi Zhang; Patrick J Carroll; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2013-11-12       Impact factor: 15.419
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