Literature DB >> 28867835

Asymmetric Synthesis of All-Carbon Quaternary Spirocycles via a Catalytic Enantioselective Allylic Alkylation Strategy.

Samantha E Shockley1, J Caleb Hethcox1, Brian M Stoltz1.   

Abstract

Rapid access to enantioenriched spirocycles possessing a 1,4-dicarbonyl moiety spanning an all-carbon quaternary stereogenic spirocenter was achieved using a masked bromomethyl vinyl ketone reagent. The developed protocol entails an enantioselective palladium-catalyzed allylic alkylation reaction followed by a one-pot unmasking/RCM sequence that provides access to the spirocyclic compounds in good yields and selectivities.

Entities:  

Keywords:  Allylic alkylation; Asymmetric catalysis; Masked bromomethyl vinyl ketone; Palladium catalysis; Spirocycle

Year:  2017        PMID： 28867835      PMCID： PMC5578629          DOI： 10.1016/j.tetlet.2017.07.022

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  20 in total

1.  Enantioselective Construction of Quaternary Stereocenters.

Authors:  Jens Christoffers; Alexander Mann
Journal:  Angew Chem Int Ed Engl       Date:  2001-12-17       Impact factor: 15.336

Review 2.  Total syntheses of natural products containing spirocarbocycles.

Authors:  Laura K Smith; Ian R Baxendale
Journal:  Org Biomol Chem       Date:  2015-10-21       Impact factor: 3.876

3.  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

4.  Catalytic enantioselective construction of quaternary stereocenters: assembly of key building blocks for the synthesis of biologically active molecules.

Authors:  Yiyang Liu; Seo-Jung Han; Wen-Bo Liu; Brian M Stoltz
Journal:  Acc Chem Res       Date:  2015-02-25       Impact factor: 22.384

5.  Enantioselective synthesis of dialkylated N-heterocycles by palladium-catalyzed allylic alkylation.

Authors:  Yoshitaka Numajiri; Gonzalo Jiménez-Osés; Bo Wang; K N Houk; Brian M Stoltz
Journal:  Org Lett       Date:  2015-02-25       Impact factor: 6.005

6.  Catalytic enantioselective synthesis of quaternary carbon stereocentres.

Authors:  Kyle W Quasdorf; Larry E Overman
Journal:  Nature       Date:  2014-12-11       Impact factor: 49.962

7.  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

8.  Enantioselective construction of α-quaternary cyclobutanones by catalytic asymmetric allylic alkylation.

Authors:  Corey M Reeves; Christian Eidamshaus; Jimin Kim; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-17       Impact factor: 15.336

9.  Intermolecular enolate heterocoupling: scope, mechanism, and application.

Authors:  Michael P DeMartino; Ke Chen; Phil S Baran
Journal:  J Am Chem Soc       Date:  2008-08-05       Impact factor: 15.419

Review 10.  Strategies for the enantioselective synthesis of spirooxindoles.

Authors:  Nicolas R Ball-Jones; Joseph J Badillo; Annaliese K Franz
Journal:  Org Biomol Chem       Date:  2012-05-14       Impact factor: 3.876
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  1 in total

Review 1.  The Allylic Alkylation of Ketone Enolates.

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

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