Literature DB >> 19645426

An asymmetric hetero-claisen approach to 3-alkyl-3-aryloxindoles.

Nicolas Duguet1, Alexandra M Z Slawin, Andrew D Smith.   

Abstract

The reaction of a chiral N-phenylnitrone derived from Garner's aldehyde with alkylarylketenes generates 3-alkyl-3-aryloxindoles directly in excellent yields and with good to excellent levels of enantioselectivity (up to 90% ee).

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Year:  2009        PMID： 19645426     DOI： 10.1021/ol901441t

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


  4 in total

1.  The palladium catalyzed asymmetric addition of oxindoles and allenes: an atom-economical versatile method for the construction of chiral indole alkaloids.

Authors:  Barry M Trost; Jia Xie; Joshua D Sieber
Journal:  J Am Chem Soc       Date:  2011-11-30       Impact factor: 15.419

2.  Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.

Authors:  Richard P Loach; Owen S Fenton; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2016-01-19       Impact factor: 15.419

3.  Pericyclic cascade with chirality transfer: reaction pathway and origin of enantioselectivity of the hetero-Claisen approach to oxindoles.

Authors:  Nihan Çelebi-Ölçüm; Yu-hong Lam; Edward Richmond; Kenneth B Ling; Andrew D Smith; Kendall N Houk
Journal:  Angew Chem Int Ed Engl       Date:  2011-10-04       Impact factor: 15.336

4.  Oxindole synthesis via polar-radical crossover of ketene-derived amide enolates in a formal [3 + 2] cycloaddition.

Authors:  Niklas Radhoff; Armido Studer
Journal:  Chem Sci       Date:  2022-03-09       Impact factor: 9.825
  4 in total

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