Literature DB >> 20961073

Stereoselective synthesis of spirooxindole amides through nitrile hydrozirconation.

Chunliang Lu1, Qing Xiao, Paul E Floreancig.   

Abstract

Spirooxindole amides can be prepared by the intramolecular addition of functionalized indoles into acylimines that are accessed from nitriles by hydrozirconation and acylation. The stereochemical outcome at the quaternary center was controlled by the steric bulk of the substituent at the 2-position of the indole unit. The products are well-suited for diversification to prepare libraries.

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Year:  2010        PMID： 20961073      PMCID： PMC2980567          DOI： 10.1021/ol102246d

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


  29 in total

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2.  Tandem intramolecular photocycloaddition-retro-Mannich fragmentation as a route to spiro[pyrrolidine-3,3'-oxindoles]. Total synthesis of (+/-)-coerulescine, (+/-)-horsfiline, (+/-)-elacomine, and (+/-)-6-deoxyelacomine.

Authors:  James D White; Yang Li; David C Ihle
Journal:  J Org Chem       Date:  2010-06-04       Impact factor: 4.354

3.  Palladium-catalyzed domino process to spirooxindoles: ligand effect on aminopalladation versus carbopalladation.

Authors:  Stéphanie Jaegli; William Erb; Pascal Retailleau; Jean-Pierre Vors; Luc Neuville; Jieping Zhu
Journal:  Chemistry       Date:  2010-05-25       Impact factor: 5.236

4.  Synthesis and evaluation of a new polymer-supported pseudoephedrine auxiliary for asymmetric alkylations on solid phase.

Authors:  Andrea M McGhee; Jean-Claude Kizirian; David J Procter
Journal:  Org Biomol Chem       Date:  2007-02-19       Impact factor: 3.876

5.  Targeting structural and stereochemical complexity by organocascade catalysis: construction of spirocyclic oxindoles having multiple stereocenters.

Authors:  Giorgio Bencivenni; Li-Yuan Wu; Andrea Mazzanti; Berardino Giannichi; Fabio Pesciaioli; Mao-Ping Song; Giuseppe Bartoli; Paolo Melchiorre
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Spiroindolones, a potent compound class for the treatment of malaria.

Authors:  Matthias Rottmann; Case McNamara; Bryan K S Yeung; Marcus C S Lee; Bin Zou; Bruce Russell; Patrick Seitz; David M Plouffe; Neekesh V Dharia; Jocelyn Tan; Steven B Cohen; Kathryn R Spencer; Gonzalo E González-Páez; Suresh B Lakshminarayana; Anne Goh; Rossarin Suwanarusk; Timothy Jegla; Esther K Schmitt; Hans-Peter Beck; Reto Brun; Francois Nosten; Laurent Renia; Veronique Dartois; Thomas H Keller; David A Fidock; Elizabeth A Winzeler; Thierry T Diagana
Journal:  Science       Date:  2010-09-03       Impact factor: 47.728

7.  Highly enantioselective construction of spiro[4H-pyran-3,3'-oxindoles] through a domino Knoevenagel/Michael/cyclization sequence catalyzed by cupreine.

Authors:  Wen-Bing Chen; Zhi-Jun Wu; Qing-Lan Pei; Lin-Feng Cun; Xiao-Mei Zhang; Wei-Cheng Yuan
Journal:  Org Lett       Date:  2010-07-16       Impact factor: 6.005

8.  Stereoselective synthesis of spirooxindoles by palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with isatins.

Authors:  Ryo Shintani; Shin-ya Hayashi; Masataka Murakami; Momotaro Takeda; Tamio Hayashi
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

Review 9.  Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents.

Authors:  Chris V Galliford; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

10.  Diastereoselection in the formation of spirocyclic oxindoles by the intramolecular Heck reaction.

Authors:  Larry E Overman; Donald A Watson
Journal:  J Org Chem       Date:  2006-03-31       Impact factor: 4.354
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  6 in total

1.  Versatile approach to α-alkoxy carbamate synthesis and stimulus-responsive alcohol release.

Authors:  R Adam Mosey; Paul E Floreancig
Journal:  Org Biomol Chem       Date:  2012-10-21       Impact factor: 3.876

2.  Stereocontrolled cyanohydrin ether synthesis through chiral Brønsted acid-mediated vinyl ether hydrocyanation.

Authors:  Chunliang Lu; Xiaoge Su; Paul E Floreancig
Journal:  J Org Chem       Date:  2013-09-04       Impact factor: 4.354

3.  Construction of a spirooxindole amide library through nitrile hydrozirconation-acylation-cyclization cascade.

Authors:  Matthew G LaPorte; Sammi Tsegay; Ki Bum Hong; Chunliang Lu; Cheng Fang; Lirong Wang; Xiang-Qun Xie; Paul E Floreancig
Journal:  ACS Comb Sci       Date:  2013-06-26       Impact factor: 3.784

4.  Complete transfer of chirality in an intramolecular, thermal [2 + 2] cycloaddition of allene-ynes to form non-racemic spirooxindoles.

Authors:  Kay M Brummond; Joshua M Osbourn
Journal:  Beilstein J Org Chem       Date:  2011-05-12       Impact factor: 2.883

5.  Homoallylic amines by reductive inter- and intramolecular coupling of allenes and nitriles.

Authors:  Peter Wipf; Marija D Manojlovic
Journal:  Beilstein J Org Chem       Date:  2011-06-17       Impact factor: 2.883

6.  Highly Efficient and Stereoselective Construction of Bispirooxindole Derivatives via a Three-Component 1,3-Dipolar Cycloaddition Reaction.

Authors:  Qin Xu; De Wang; Yin Wei; Min Shi
Journal:  ChemistryOpen       Date:  2014-06-18       Impact factor: 2.911
  6 in total

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