Literature DB >> 27210481

Revisited Mechanistic Implications of the Joullié-Ugi Three-Component Reaction.

Akira Katsuyama1, Akira Matsuda1,2, Satoshi Ichikawa1,2.   

Abstract

The effect of the solvent on the diastereoselectivity of the Joullié-Ugi three-component reaction (JU-3CR) using an α-substituted five-membered cyclic imine is revisited. The cis and trans isomers were generated in toluene and HFIP, respectively. Hammett analysis of the JU-3CR suggests the presence of two reaction mechanisms.

Entities:  

Year:  2016        PMID： 27210481     DOI： 10.1021/acs.orglett.6b00827

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


  3 in total

Review 1.  Isocyanide-Based Multicomponent Reactions in Water: Advanced Green Tools for the Synthesis of Heterocyclic Compounds.

Authors:  Siamak Javanbakht; Mohammad Taghi Nazeri; Hassan Farhid; Tahereh Nasiriani; Vida Khodkari; Ahmad Shaabani
Journal:  Top Curr Chem (Cham)       Date:  2022-09-22

2.  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

3.  Multi-Gram Synthesis of Enantiopure 1,5-Disubstituted Tetrazoles Via Ugi-Azide 3-Component Reaction.

Authors:  Pietro Capurro; Lisa Moni; Andrea Galatini; Christian Mang; Andrea Basso
Journal:  Molecules       Date:  2018-10-25       Impact factor: 4.411
  3 in total

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