Supramolecular Catalysis with Chiral Mono- and Bis-(Thio)Urea-Derivatives-Reference-Cited by-同舟云学术

Supramolecular Catalysis with Chiral Mono- and Bis-(Thio)Urea-Derivatives

Published:2024-03-26 Issue:2 Volume:5 Page:32-45
ISSN:2673-401X
Container-title:Organics
language:en
Short-container-title:Organics

Author:

Iuliano Veronica¹^ORCID,Della Sala Paolo¹^ORCID,Talotta Carmen¹^ORCID,De Rosa Margherita¹^ORCID,Gaeta Carmine¹^ORCID,Neri Placido¹^ORCID,Soriente Annunziata¹

Affiliation:

1. Dipartimento di Chimica e Biologia “A. Zambelli”, Università di Salerno, Via Giovanni Paolo II, Fisciano, I-84084 Salerno, Italy

Abstract

Chiral mono- and bis-(thio)urea supramolecular organocatalysts were studied in the enantioselective vinylogous addition reaction of 2-trimethylsilyloxyfuran (TMSOF) to carbonylic compounds; the corresponding chiral γ-hydroxymethyl-butenolides are obtained in good yields and with high enantiomeric excesses. The catalyst structure, as well as the reaction conditions, strongly influence the efficiency of the reaction. The conformational features of mono(thio)urea catalysts 2 and 3 and bis(thio)urea catalysts 7 and 8 were investigated by DFT calculations along with the structure of their complexes with benzaldehyde. Natural Bond Orbital (NBO) and Non-Covalent Interaction (NCI) calculations provided useful information concerning the activating H-bonding interactions in the complexes.

Funder

UNIVERSITY of SALERNO

Publisher

MDPI AG

Link

https://www.mdpi.com/2673-401X/5/2/3/pdf

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