Literature DB >> 22545918

Dinuclear zinc catalyzed asymmetric spirannulation reaction: an umpolung strategy for formation of α-alkylated-α-hydroxyoxindoles.

Barry M Trost1, Keiichi Hirano.   

Abstract

A highly diastereo- and enantioselective formal [3 + 2] cycloaddition of α,β-unsaturated esters and 3-hydroxyoxindoles catalyzed by a dinuclear zinc-ProPhenol complex is reported. The stereoselective Michael additions of 3-hydroxyoxindoles and the subsequent transesterifications afford spirocyclic δ-lactones.

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Year:  2012        PMID： 22545918     DOI： 10.1021/ol300577y

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


  7 in total

Review 1.  Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones.

Authors:  Bin Mao; Martín Fañanás-Mastral; Ben L Feringa
Journal:  Chem Rev       Date:  2017-06-22       Impact factor: 60.622

2.  Dinuclear zinc-ProPhenol-catalyzed enantioselective α-hydroxyacetate aldol reaction with activated ester equivalents.

Authors:  Barry M Trost; David J Michaelis; Mihai I Truica
Journal:  Org Lett       Date:  2013-08-15       Impact factor: 6.005

3.  ProPhenol-catalyzed asymmetric additions by spontaneously assembled dinuclear main group metal complexes.

Authors:  Barry M Trost; Mark J Bartlett
Journal:  Acc Chem Res       Date:  2015-02-04       Impact factor: 22.384

4.  N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate.

Authors:  Xiang-Yu Chen; Kun-Quan Chen; De-Qun Sun; Song Ye
Journal:  Chem Sci       Date:  2016-11-09       Impact factor: 9.825

5.  Synthesis of (Z)-3-[amino(phenyl)methylidene]-1,3-dihydro-2H-indol-2-ones using an Eschenmoser coupling reaction.

Authors:  Lukáš Marek; Lukáš Kolman; Jiří Váňa; Jan Svoboda; Jiří Hanusek
Journal:  Beilstein J Org Chem       Date:  2021-02-23       Impact factor: 2.883

6.  Synthesis of spiro[indoline-3,1'-quinolizines] and spiro[indoline-3, 4'-pyrido[1,2-a]quinolines] via three-component reactions of azaarenes, acetylenedicarboxylate, and 3-methyleneoxindoles.

Authors:  Jing Sun; Hui Gong; Yan Sun; Chao-Guo Yan
Journal:  Mol Divers       Date:  2013-07-19       Impact factor: 2.943

7.  Reductive Coupling of Acrylates with Ketones and Ketimines by a Nickel-Catalyzed Transfer-Hydrogenative Strategy.

Authors:  Craig S Buxton; David C Blakemore; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-04       Impact factor: 15.336
  7 in total

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