Literature DB >> 26986694

Diastereoselective Passerini Reaction of Biobased Chiral Aldehydes: Divergent Synthesis of Various Polyfunctionalized Heterocycles.

Lisa Moni1, Luca Banfi1, Andrea Basso1, Elisa Martino1, Renata Riva1.   

Abstract

Lewis acid catalyzed Passerini reactions on chiral aldehydes derived from desymmetrized erythritol take place with unprecedented diastereoselectivity. The resulting adducts have been selectively and efficiently converted into a variety of densely functionalized, polyoxygenated heterocycles.

Entities:  

Year:  2016        PMID： 26986694     DOI： 10.1021/acs.orglett.6b00487

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


  6 in total

1.  Stereodivergent access to all four stereoisomers of chiral tetrahydrobenzo[f][1,4]oxazepines, through highly diastereoselective multicomponent Ugi-Joullié reaction.

Authors:  Alessandro Pinna; Andrea Basso; Chiara Lambruschini; Lisa Moni; Renata Riva; Valeria Rocca; Luca Banfi
Journal:  RSC Adv       Date:  2020-01-03       Impact factor: 3.361

2.  Stereoselective Synthesis of Functionalized Bicyclic Scaffolds by Passerini 3-Center-2-Component Reactions of Cyclic Ketoacids.

Authors:  Răzvan C Cioc; Verónica Estévez; Daan J van der Niet; Christophe M L Vande Velde; Nikolaus G Turrini; Mélanie Hall; Kurt Faber; Eelco Ruijter; Romano V A Orru
Journal:  European J Org Chem       Date:  2017-03-08

Review 3.  The 100 facets of the Passerini reaction.

Authors:  Luca Banfi; Andrea Basso; Chiara Lambruschini; Lisa Moni; Renata Riva
Journal:  Chem Sci       Date:  2021-09-30       Impact factor: 9.825

4.  Silica gel-immobilised chiral 1,2-benzenedisulfonimide: a Brønsted acid heterogeneous catalyst for enantioselective multicomponent Passerini reaction.

Authors:  Achille Antenucci; Francesco Marra; Stefano Dughera
Journal:  RSC Adv       Date:  2021-07-29       Impact factor: 4.036

5.  Synthesis of Polyoxygenated Heterocycles by Diastereoselective Functionalization of a Bio-Based Chiral Aldehyde Exploiting the Passerini Reaction.

Authors:  Gabriella Vitali Forconesi; Luca Banfi; Andrea Basso; Chiara Lambruschini; Lisa Moni; Renata Riva
Journal:  Molecules       Date:  2020-07-15       Impact factor: 4.411

6.  C-Linked Glycomimetic Libraries Accessed by the Passerini Reaction.

Authors:  Kristina Vlahoviček-Kahlina; Josipa Suć Sajko; Ivanka Jerić
Journal:  Int J Mol Sci       Date:  2019-12-10       Impact factor: 5.923
  6 in total

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