Literature DB >> 18540630

Stereoselective synthesis of acetoacetate-derived enol triflates.

David Babinski1, Omid Soltani, Doug E Frantz.   

Abstract

A highly stereoselective method for preparing ( Z)- and ( E)-enol triflates derived from substituted acetoacetate derivatives is described. The salient feature of this methodology is the use of Schotten-Baumann-type conditions to control enolate geometry using either aqueous LiOH ( Z-selective) or aqueous (Me)(4)NOH ( E-selective) in combination with triflic anhydride to provide a practical and predictable approach to these valuable substrates.

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Year:  2008        PMID： 18540630     DOI： 10.1021/ol8010002

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


  11 in total

1.  An organocatalytic asymmetric Nazarov cyclization.

Authors:  Ashok K Basak; Naoyuki Shimada; William F Bow; David A Vicic; Marcus A Tius
Journal:  J Am Chem Soc       Date:  2010-06-23       Impact factor: 15.419

2.  Diastereospecific nazarov cyclization of fully substituted dienones: generation of vicinal all-carbon-atom quaternary stereocenters.

Authors:  Anais Jolit; Saleta Vazquez-Rodriguez; Glenn P A Yap; Marcus A Tius
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-03       Impact factor: 15.336

3.  Synthesis of substituted pyrazoles via tandem cross-coupling/electrocyclization of enol triflates and diazoacetates.

Authors:  David J Babinski; Hector R Aguilar; Raymond Still; Doug E Frantz
Journal:  J Org Chem       Date:  2011-06-27       Impact factor: 4.354

4.  Formation of Chiral Allylic Ethers via an Enantioselective Palladium-Catalyzed Alkenylation of Acyclic Enol Ethers.

Authors:  Harshkumar H Patel; Matthew B Prater; Scott O Squire; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2018-04-27       Impact factor: 15.419

5.  Total synthesis and structure-activity relationship study of the potent cAMP signaling agonist (-)-alotaketal A.

Authors:  Jinhua Huang; Jessica R Yang; Jin Zhang; Jiong Yang
Journal:  Org Biomol Chem       Date:  2013-04-12       Impact factor: 3.876

6.  Pd-catalyzed asymmetric β-hydride elimination en route to chiral allenes.

Authors:  Ian T Crouch; Robynne K Neff; Doug E Frantz
Journal:  J Am Chem Soc       Date:  2013-03-19       Impact factor: 15.419

7.  Selective one-pot synthesis of allenyl and alkynyl esters from beta-ketoesters.

Authors:  Pradip Maity; Salvatore D Lepore
Journal:  J Org Chem       Date:  2009-01-02       Impact factor: 4.354

8.  Total synthesis of the potent cAMP signaling agonist (-)-alotaketal A.

Authors:  Jinhua Huang; Jessica R Yang; Jin Zhang; Jiong Yang
Journal:  J Am Chem Soc       Date:  2012-05-16       Impact factor: 15.419

9.  Studies toward brevisulcenal F via convergent strategies for marine ladder polyether synthesis.

Authors:  Matthew Katcher; Timothy F Jamison
Journal:  Tetrahedron       Date:  2018-02-02       Impact factor: 2.457

10.  Chemoenzymatic asymmetric synthesis of pregabalin precursors via asymmetric bioreduction of β-cyanoacrylate esters using ene-reductases.

Authors:  Christoph K Winkler; Dorina Clay; Simon Davies; Pat O'Neill; Paul McDaid; Sebastien Debarge; Jeremy Steflik; Mike Karmilowicz; John W Wong; Kurt Faber
Journal:  J Org Chem       Date:  2013-01-28       Impact factor: 4.354
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