Literature DB >> 34854689

Enantioselective Indole Insertion Reactions of α-Carbonyl Sulfoxonium Ylides.

Alexandria N Leveille1, Radell Echemendía2, Anita E Mattson1, Antonio C B Burtoloso2.   

Abstract

The first example of organocatalytic enantioselective C-H insertion reactions of indoles and sulfoxonium ylides is reported. Under the influence of phosphoric acid catalysis, levels of enantiocontrol in the range of 20-93% ee and moderate yields (up to 50%) were achieved for 29 examples in formal C-H insertion reactions of free indoles and α-carbonyl sulfoxonium ylides. No nitrogen protection on the indole is necessary.

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Year:  2021        PMID: 34854689     DOI: 10.1021/acs.orglett.1c03627

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


  2 in total

Review 1.  Asymmetric transformations from sulfoxonium ylides.

Authors:  Clarice A D Caiuby; Lucas G Furniel; Antonio C B Burtoloso
Journal:  Chem Sci       Date:  2021-12-08       Impact factor: 9.825

2.  Sulfoxonium Ylides in Aminocatalysis: An Enantioselective Entry to Cyclopropane-Fused Chromanol Structures.

Authors:  Giorgiana Denisa Bisag; Pietro Pecchini; Michele Mancinelli; Mariafrancesca Fochi; Luca Bernardi
Journal:  Org Lett       Date:  2022-07-20       Impact factor: 6.072

  2 in total

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