Literature DB >> 22215069

Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective Ugi multicomponent reaction.

Valentina Cerulli1, Luca Banfi, Andrea Basso, Valeria Rocca, Renata Riva.   

Abstract

A highly diastereoselective Ugi reaction involving a chiral cyclic imine, two enantiomerically pure isocyanides and various carboxylic acids was employed for the synthesis of polyfunctionalized pyrrolidines. Both chiral substrates have been efficiently prepared by chemoenzymatic methodologies from readily available achiral substrates. This highly convergent approach can find an application in the fragment-based drug discovery process.

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Year:  2012        PMID: 22215069     DOI: 10.1039/c1ob06632c

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  4 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

Review 2.  Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics.

Authors:  Gijs Koopmanschap; Eelco Ruijter; Romano Va Orru
Journal:  Beilstein J Org Chem       Date:  2014-03-04       Impact factor: 2.883

3.  Diastereoselective Ugi reaction of chiral 1,3-aminoalcohols derived from an organocatalytic Mannich reaction.

Authors:  Samantha Caputo; Andrea Basso; Lisa Moni; Renata Riva; Valeria Rocca; Luca Banfi
Journal:  Beilstein J Org Chem       Date:  2016-01-26       Impact factor: 2.883

4.  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

  4 in total

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