Literature DB >> 19719185

Stereocontrolled synthesis of spirooxindoles through Lewis acid-promoted [5 + 2]-annulation of chiral silyl alcohols.

Yun Zhang1, James S Panek.   

Abstract

The enantioselective synthesis of stereochemically and structurally diverse spirocyclic oxindoles by [5 + 2]-annulation of chiral crotylsilanes bearing a primary alcohol is described. The annulation products were further elaborated to polycyclic oxindoles by Pd(0) catalysis.

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Year:  2009        PMID： 19719185      PMCID： PMC2761606          DOI： 10.1021/ol901202t

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


  21 in total

1.  Suspected blue canary grass (Phalaris coerulescens) poisoning of horses.

Authors:  S M Colegate; N Anderton; J Edgar; C A Bourke; R N Oram
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2.  Solid-phase synthesis and asymmetric reactions of polymer-supported highly enantioenriched allylsilanes.

Authors:  M Suginome; T Iwanami; Y Ito
Journal:  J Am Chem Soc       Date:  2001-05-09       Impact factor: 15.419

3.  Total synthesis of (-)-apicularen A.

Authors:  Qibin Su; James S Panek
Journal:  J Am Chem Soc       Date:  2004-03-03       Impact factor: 15.419

4.  Stereocontrolled [4+2]-annulation accessing dihydropyrans: synthesis of the C1a-C10 fragment of kendomycin.

Authors:  Jason T Lowe; James S Panek
Journal:  Org Lett       Date:  2005-04-14       Impact factor: 6.005

5.  Effects of Uncaria tomentosa total alkaloid and its components on experimental amnesia in mice: elucidation using the passive avoidance test.

Authors:  A F Mohamed; K Matsumoto; K Tabata; H Takayama; M Kitajima; H Watanabe
Journal:  J Pharm Pharmacol       Date:  2000-12       Impact factor: 3.765

6.  Rhynchophylline and isorhynchophylline inhibit NMDA receptors expressed in Xenopus oocytes.

Authors:  Tai-Hyun Kang; Yukihisa Murakami; Kinzo Matsumoto; Hiromitsu Takayama; Mariko Kitajima; Norio Aimi; Hiroshi Watanabe
Journal:  Eur J Pharmacol       Date:  2002-11-22       Impact factor: 4.432

Review 7.  Paraherquamides, brevianamides, and asperparalines: laboratory synthesis and biosynthesis. An interim report.

Authors:  Robert M Williams; Rhona J Cox
Journal:  Acc Chem Res       Date:  2003-02       Impact factor: 22.384

8.  Organosilanes in synthesis: application to an enantioselective synthesis of methyl-l-callipeltose.

Authors:  Hongbing Huang; James S Panek
Journal:  Org Lett       Date:  2003-05-29       Impact factor: 6.005

9.  Multicomponent reactions of diazoamides: diastereoselective synthesis of mono- and bis-spirofurooxindoles.

Authors:  Sengodagounder Muthusamy; Chidambaram Gunanathan; Munirathinam Nethaji
Journal:  J Org Chem       Date:  2004-08-20       Impact factor: 4.354

10.  Highly enantioenriched tetrahydropyridines from chiral organosilanes: application to the synthesis of quinolizidine alkaloid (-)-217A.

Authors:  Hongbing Huang; Thomas F Spande; James S Panek
Journal:  J Am Chem Soc       Date:  2003-01-22       Impact factor: 15.419
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  9 in total

1.  Stereoselective synthesis of tertiary ethers through geometric control of highly substituted oxocarbenium ions.

Authors:  Lei Liu; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-09       Impact factor: 15.336

2.  Enantioselective syntheses of syn- and anti-β-hydroxyallylsilanes via allene hydroboration-aldehyde allylboration reactions.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2011-03-16       Impact factor: 6.005

3.  Stereoselective synthesis of spirooxindole amides through nitrile hydrozirconation.

Authors:  Chunliang Lu; Qing Xiao; Paul E Floreancig
Journal:  Org Lett       Date:  2010-10-20       Impact factor: 6.005

4.  Highly stereoselective Brønsted acid catalyzed synthesis of spirooxindole pyrans.

Authors:  Jingqi Wang; Erika A Crane; Karl A Scheidt
Journal:  Org Lett       Date:  2011-05-18       Impact factor: 6.005

5.  Multicomponent reaction discovery: three-component synthesis of spirooxindoles.

Authors:  Bo Liang; Srinivas Kalidindi; John A Porco; Corey R J Stephenson
Journal:  Org Lett       Date:  2010-02-05       Impact factor: 6.005

Review 6.  Molecular diversity of spirooxindoles. Synthesis and biological activity.

Authors:  Tetyana L Pavlovska; Ruslan Gr Redkin; Victoria V Lipson; Dmytro V Atamanuk
Journal:  Mol Divers       Date:  2015-09-29       Impact factor: 2.943

7.  (Z)-1-Acetyl-3-[2-oxo-1-phenyl-2-(3-pyrid-yl)ethyl-idene]indolin-2-one.

Authors:  Hoong-Kun Fun; Jia Hao Goh; Haitao Yu; Yan Zhang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-08-11

8.  3',7',7'-Trimethyl-1'-phenyl-5',6',7',8'-tetra-hydro-spiro-[indoline-3,4'-(1H,4H-pyrazolo-[3,4-b]chromene)]-2,5'-dione.

Authors:  Li-Qin Zhao; Bin Li; Yi-Qun Li
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-11-10

9.  An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective RhII-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes.

Authors:  Kevin X Rodriguez; Tara C Pilato; Brandon L Ashfeld
Journal:  Chem Sci       Date:  2018-02-19       Impact factor: 9.825
  9 in total

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