Literature DB >> 24999286

Palladium-catalyzed decarboxylative allylic alkylation of diastereomeric β-ketoesters.

Sandy Ma1, Corey M Reeves1, Robert A Craig1, Brian M Stoltz1.   

Abstract

The palladium-catalyzed decarboxylative allylic alkylation of diastereomeric β-ketoesters derived from 4-tert-butylcyclohexanone is described. These experiments were performed to elucidate our understanding of stereoablative enantioconvergent catalysis. A detailed analysis of the product distribution, including stereochemical outcome of the products, is included. These studies also reveal an interesting example of selectivity that is governed by competing modes of substrate and catalyst control.

Entities:  

Keywords:  Alkylation; Allylic; Decarboxylative; Ketoesters; Palladium

Year:  2014        PMID： 24999286      PMCID： PMC4078409          DOI： 10.1016/j.tet.2014.03.042

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  6 in total

1.  Deracemization of quaternary stereocenters by Pd-catalyzed enantioconvergent decarboxylative allylation of racemic beta-ketoesters.

Authors:  Justin T Mohr; Douglas C Behenna; Andrew M Harned; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2005-10-28       Impact factor: 15.336

2.  The inner-sphere process in the enantioselective Tsuji allylation reaction with (S)-t-Bu-phosphinooxazoline ligands.

Authors:  John A Keith; Douglas C Behenna; Justin T Mohr; Sandy Ma; Smaranda C Marinescu; Jonas Oxgaard; Brian M Stoltz; William A Goddard
Journal:  J Am Chem Soc       Date:  2007-09-08       Impact factor: 15.419

3.  Total synthesis of the L-hexoses.

Authors:  S Y Ko; A W Lee; S Masamune; L A Reed; K B Sharpless; F J Walker
Journal:  Science       Date:  1983-05-27       Impact factor: 47.728

4.  Enantioselective decarboxylative alkylation reactions: catalyst development, substrate scope, and mechanistic studies.

Authors:  Douglas C Behenna; Justin T Mohr; Nathaniel H Sherden; Smaranda C Marinescu; Andrew M Harned; Kousuke Tani; Masaki Seto; Sandy Ma; Zoltán Novák; Michael R Krout; Ryan M McFadden; Jennifer L Roizen; John A Enquist; David E White; Samantha R Levine; Krastina V Petrova; Akihiko Iwashita; Scott C Virgil; Brian M Stoltz
Journal:  Chemistry       Date:  2011-11-14       Impact factor: 5.236

5.  The reaction mechanism of the enantioselective Tsuji allylation: inner-sphere and outer-sphere pathways, internal rearrangements, and asymmetric C-C bond formation.

Authors:  John A Keith; Douglas C Behenna; Nathaniel Sherden; Justin T Mohr; Sandy Ma; Smaranda C Marinescu; Robert J Nielsen; Jonas Oxgaard; Brian M Stoltz; William A Goddard
Journal:  J Am Chem Soc       Date:  2012-11-06       Impact factor: 15.419

6.  Unusual allylpalladium carboxylate complexes: identification of the resting state of catalytic enantioselective decarboxylative allylic alkylation reactions of ketones.

Authors:  Nathaniel H Sherden; Douglas C Behenna; Scott C Virgil; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
  6 in total
  3 in total

1.  Development of a catalytic enantioselective synthesis of the guanacastepene and heptemerone tricyclic core.

Authors:  Andrew M Harned; Brian M Stoltz
Journal:  Tetrahedron       Date:  2019-02-27       Impact factor: 2.457

2.  Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.

Authors:  Vikram Bhat; Eric R Welin; Xuelei Guo; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-02-06       Impact factor: 60.622

3.  3-{(E)-[4-(4-Hy-droxy-3-meth-oxy-phen-yl)butan-2-yl-idene]amino}-1-phenyl-urea: crystal structure and Hirshfeld surface analysis.

Authors:  Ming Yueh Tan; Karen A Crouse; Thahira B S A Ravoof; Mukesh M Jotani; Edward R T Tiekink
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2018-01-01
  3 in total

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