Literature DB >> 23112107

Highly enantio- and diastereoselective generation of two quaternary centers in spirocyclopropanation of oxindole derivatives.

Artur Noole1, Natalia S Sucman, Mikhail A Kabeshov, Tõnis Kanger, Fliur Z Macaev, Andrei V Malkov.   

Abstract

Spirocyclopropanes: Only one out of eight possible stereoisomers was obtained in the asymmetric cascade cyclopropanation of alkylidene oxindoles with ethyl 2-chloroacetoacetate. Improved catalyst design ensured that spirocyclopropyl oxindoles featuring two quaternary centers were synthesized in high yield and high enantio- and diastereoselectivity (see scheme).
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID: 23112107     DOI: 10.1002/chem.201203099

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  4 in total

Review 1.  Recent Advances on the Total Syntheses of Communesin Alkaloids and Perophoramidine.

Authors:  Barry M Trost; Maksim Osipov
Journal:  Chemistry       Date:  2015-09-10       Impact factor: 5.236

2.  Palladium-catalyzed asymmetric construction of vicinal all-carbon quaternary stereocenters and its application to the synthesis of cyclotryptamine alkaloids.

Authors:  Barry M Trost; Maksim Osipov
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-03       Impact factor: 15.336

3.  Nickel(ii)-catalyzed enantioselective cyclopropanation of 3-alkenyl-oxindoles with phenyliodonium ylide via free carbene.

Authors:  Jing Guo; Yangbin Liu; Xiangqiang Li; Xiaohua Liu; Lili Lin; Xiaoming Feng
Journal:  Chem Sci       Date:  2016-01-04       Impact factor: 9.825

Review 4.  Catalytic enantioselective construction of vicinal quaternary carbon stereocenters.

Authors:  Feng Zhou; Lei Zhu; Bo-Wen Pan; Yang Shi; Yun-Lin Liu; Jian Zhou
Journal:  Chem Sci       Date:  2020-07-28       Impact factor: 9.825

  4 in total

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