Literature DB >> 25245762

A cation-directed two-component cascade approach to enantioenriched pyrroloindolines.

Jamie R Wolstenhulme1, Alex Cavell, Matija Gredičak, Russell W Driver, Martin D Smith.   

Abstract

A cascade approach to complex pyrroloindolines bearing all-carbon quaternary stereocentres has been developed. This two-component process uses a chiral ammonium salt to control diastereo- and enantioselectivity in the addition of isocyanides to functionalized alkenes to afford pyrroloindolines with up to three stereocentres. A mechanistic proposal involving intramolecular hydrogen bond activation of the isocyanide is described.

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Year:  2014        PMID: 25245762     DOI: 10.1039/c4cc06683a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  3 in total

Review 1.  Intramolecular Hydrogen-Bond Activation: Strategies, Benefits, and Influence in Catalysis.

Authors:  Andrea Guerrero-Corella; Alberto Fraile; José Alemán
Journal:  ACS Org Inorg Au       Date:  2022-02-03

2.  On the prevalence of bridged macrocyclic pyrroloindolines formed in regiodivergent alkylations of tryptophan.

Authors:  Tristin E Rose; Brice H Curtin; Kenneth V Lawson; Adam Simon; K N Houk; Patrick G Harran
Journal:  Chem Sci       Date:  2016-03-09       Impact factor: 9.825

3.  Design of chiral urea-quaternary ammonium salt hybrid catalysts for asymmetric reactions of glycine Schiff bases.

Authors:  Maximilian Tiffner; Johanna Novacek; Alfonso Busillo; Katharina Gratzer; Antonio Massa; Mario Waser
Journal:  RSC Adv       Date:  2015-08-28       Impact factor: 3.361

  3 in total

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