Literature DB >> 23203457

Catalytic diastereo- and enantioselective annulations between transient nitrosoalkenes and indoles.

Yu Zhang1, David Stephens, Graciela Hernandez, Rosalinda Mendoza, Oleg V Larionov.   

Abstract

Caught in transition: an efficient catalytic system is the key to the successful development of the first highly diastereo- and enantioselective annulation reaction between indoles and transient nitrosoalkenes. This robust reaction affords structurally unique architectures with up to three new chiral centers. The products can be readily elaborated into other indoline-based chiral heterocyclic motifs, including those of pyrrolidinoindoline alkaloids.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID: 23203457     DOI: 10.1002/chem.201203435

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


  6 in total

1.  Copper-catalyzed diastereoselective arylation of tryptophan derivatives: total synthesis of (+)-naseseazines A and B.

Authors:  Madeleine E Kieffer; Kangway V Chuang; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2013-04-03       Impact factor: 15.419

2.  Recent developments in the catalytic, asymmetric construction of pyrroloindolines bearing all-carbon quaternary stereocenters.

Authors:  Lindsay M Repka; Sarah E Reisman
Journal:  J Org Chem       Date:  2013-12-02       Impact factor: 4.354

3.  Insights into the structural patterns of the antileishmanial activity of bi- and tricyclic N-heterocycles.

Authors:  Lizzi Herrera; David E Stephens; Abigail D'Avila; Kathryn G George; Hadi Arman; Yu Zhang; George Perry; Ricardo Lleonart; Oleg V Larionov; Patricia L Fernández
Journal:  Org Biomol Chem       Date:  2016-07-04       Impact factor: 3.876

4.  C7-derivatization of C3-alkylindoles including tryptophans and tryptamines.

Authors:  Richard P Loach; Owen S Fenton; Kazuma Amaike; Dustin S Siegel; Erhan Ozkal; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2014-11-10       Impact factor: 4.354

5.  Rapid assembly of functionalised spirocyclic indolines by palladium-catalysed dearomatising diallylation of indoles with allyl acetate.

Authors:  Persis Dhankher; Laure Benhamou; Tom D Sheppard
Journal:  Chemistry       Date:  2014-08-29       Impact factor: 5.236

Review 6.  Conjugated nitrosoalkenes as Michael acceptors in carbon-carbon bond forming reactions: a review and perspective.

Authors:  Yaroslav Dmitrievich Boyko; Valentin Sergeevich Dorokhov; Alexey Yu Sukhorukov; Sema Leibovich Ioffe
Journal:  Beilstein J Org Chem       Date:  2017-10-23       Impact factor: 2.883

  6 in total

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