Vincenzo Zambrano

Istituto di Chimica Biomolecolare

Author Statistics

Papers

Citation

H-Index

i-10 index

Research Trends

Author Order

Document Type

Co-Authors

Gloria Rassu

Istituto di Chimica Biomolecolare

Franca Zanardi

University of Parma

Lucia Battistini

University of Parma

Claudio Curti

University of Parma

Giovanni Casiraghi

University of Parma

Giorgio Pelosi

University of Parma

Luigi Pinna

University of Sassari

Andrea Sartori

University of Parma

Luciana Auzzas

University of Sassari

Lorenzo A. Pinna

University of Padua

Cooperative Institutions

University of Sassari

University of Parma

Istituto di Chimica Biomolecolare

University of Florence

Tecnologie Avanzate (Italy)

Sigma Tau (Italy)

Universitat Politècnica de Catalunya

Istituto di Farmacologia Traslazionale

University Hospitals Parma Medical Center

University of Palermo

Author Statistics

Papers

Citation

H-Index

i-10 index

Research Field

ChemInform Abstract: Exploring the Vinylogous Reactivity of Cyclohexenylidene Malononitriles: Switchable Regioselectivity in the Organocatalytic Asymmetric Addition to Enals Giving Highly Enantioenriched Carbabicyclic Structures.

ChemInform (2015)

Luca Dell’Amico Gloria Rassu Vincenzo Zambrano Andrea Sartori Claudio Curti

Abstract A two‐step, one‐pot sequence under chiral amine—NHC catalysis allows the approach to spiro[4.5]decanone structures in a diastereoselective manner with high e.e.

Reactivity

Sequence (biology)

10.1002/chin.201509070

Cite

Citations (0)

CCDC 757775: Experimental Crystal Structure Determination

The Cambridge Structural Database (2011)

Claudio Curti Beatrice Ranieri Lucia Battistini Gloria Rassu Vincenzo Zambrano

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/cctfjc3

Cite

Citations (0)

Variable Strategy toward Carbasugars and Relatives. 5.¹ Focus on Preparation of Chiral Nonracemic Medium-Sized Carbocycles

The Journal of Organic Chemistry (2003)

Gloria Rassu Luciana Auzzas Luigi Pinna Vincenzo Zambrano Franca Zanardi

The feasibility of sequential vinylogous aldol (intermolecular)/silylative aldol (intramolecular) addition reactions involving furan- and pyrrole-based dienoxysilanes, 6 and 12, in the synthesis of carbasugar frameworks is illustrated by the preparation of the scantily investigated carbaseptanose and carbaoctanose representatives of this class of compounds. The target compounds, 1, 2, 3, ent-2, ent-3, and 4, were obtained from readily available carbohydrate precursors (5 and 19) in yields of 21-30% over 8-12 steps. The irreversible silylative ring-closing aldolisation of gamma-substituted dihydro-5H-furan-2-one and pyrrolidin-2-one aldehydes (9, 16, ent-16, and 22) driven by the TBSOTf/Pr(i)(2)EtN Lewis acid-Lewis base couple was shown to be a practical, diastereoselective maneuver to forge the densely functionalized, medium-sized core carbocycles.

Furan

Aldol reaction

Pyrrole

10.1021/jo0344539

Cite

Citations (36)

ChemInform Abstract: Direct Regio‐, Diastereo‐, and Enantioselective Vinylogous Michael Addition of Prochiral 3‐Alkylideneoxindoles to Nitroolefins.

ChemInform (2013)

Gloria Rassu Vincenzo Zambrano Luigi Pinna Claudio Curti Lucia Battistini

Abstract The asymmetric Michael addition of prochiral 3‐alkylideneoxindoles to nitroolefins is realized in the presence of a dihydroquinine derived thiourea catalyst.

Michael reaction

10.1002/chin.201345114

Cite

Citations (0)

CCDC 1047357: Experimental Crystal Structure Determination

The Cambridge Structural Database (2015)

Nicoletta Brindani Gloria Rassu Luca Dell’Amico Vincenzo Zambrano Lorenzo A. Pinna

10.5517/cc144vqv

Cite

Citations (0)

Direct Regio‐, Diastereo‐, and Enantioselective Vinylogous Michael Addition of Prochiral 3‐Alkylideneoxindoles to Nitroolefins

Advanced Synthesis & Catalysis (2013)

Gloria Rassu Vincenzo Zambrano Luigi Pinna Claudio Curti Lucia Battistini

Abstract 3‐Alkylidene‐2‐oxindoles represent a simple, yet enabling subfamily of indole alkaloids, and their ability to react as electron‐poor acceptors has largely been investigated. In contrast, their utility as pronucleophilic synthons remains elusive. In this context, the present article describes the successful execution of the direct, organocatalytic asymmetric Michael addition of prochiral 3‐alkylideneoxindoles to nitroolefins. A variety of γ‐substituted alkylideneoxindoles carrying two stereocenters at both the γ‐ and δ‐carbon sites was assembled with excellent stereoselectivity and without olefin isomerization or stereochemical ablation.

Stereocenter

Michael reaction

Synthon

10.1002/adsc.201300168

Cite

Citations (51)

Bifunctional Cinchona Alkaloid/Thiourea Catalyzes Direct and Enantioselective Vinylogous Michael Addition of 3‐Alkylidene Oxindoles to Nitroolefins

Angewandte Chemie International Edition (2012)

Claudio Curti Gloria Rassu Vincenzo Zambrano Luigi Pinna Giorgio Pelosi

Vinylogy: Advances in asymmetric catalysis using the bifunctional cinchona alkaloid/thioureas enabled an umpolung of the classical Cβ reactivity of 3-alkylidene oxindoles, thus allowing the development of the first and sole example of a direct, organocatalytic asymmetric vinylogous Michael (AVM) reaction with nitroolefins. Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

Cinchona

Umpolung

Michael reaction

Cinchona Alkaloids

Reactivity

10.1002/anie.201202027

Cite

Citations (119)

Unlocking Access to Enantiopure Fused Uracils by Chemodivergent [4+2] Cross‐Cycloadditions: DFT‐Supported Homo‐Synergistic Organocatalytic Approach

Angewandte Chemie (2020)

Claudio Curti Gloria Rassu Marco Lombardo Vincenzo Zambrano Luigi Pinna

Abstract The discovery of chemical methods enabling the construction of carbocycle‐fused uracils which embody a three‐dimensional and functional‐group‐rich architecture is a useful tool in medicinal chemistry oriented synthesis. In this work, an unprecedented amine‐catalyzed [4+2] cross‐cycloaddition is documented; it involves remotely enolizable 6‐methyluracil‐5‐carbaldehydes and β‐aryl enals, and chemoselectively produces two novel bicyclic and tricyclic fused uracil chemotypes in good yields with a maximum level of enantiocontrol. In‐depth mechanistic investigations and control experiments support an intriguing homo‐synergistic organocatalytic approach, where the same amine organocatalyst concomitantly engages both aldehyde partners in a stepwise eliminative [4+2] cycloaddition, whose vinylogous iminium ion intermediate product may diverge—depending upon conditions—to either bicyclic targets by hydrolysis or tricyclic products by a second homo‐synergistic trienamine‐mediated stepwise [4+2] cycloaddition.

Enantiopure drug

Iminium

Uracil

10.1002/ange.202007509

Cite

Citations (5)

Uncatalyzed, Diastereoselective Vinylogous Mukaiyama Aldol Reactions on Aqueous Media: Pyrrole vs Furan 2-Silyloxy Dienes

The Journal of Organic Chemistry (2010)

Claudio Curti Lucia Battistini Franca Zanardi Gloria Rassu Vincenzo Zambrano

The first uncatalyzed, diastereoselective vinylogous Mukaiyama aldol reaction is reported, between pyrrole/furan-based dienoxy silanes and aromatic aldehydes on salty water/methanol medium, at almost human body temperature, under ultrasonic irradiation. With pyrrole dienes the reaction is anti-selective, while that of furan dienes is syn-selective. The dual role of water as both reaction medium and promoter is highlighted.

Furan

Aldol reaction

Pyrrole

Aqueous medium

Silanes

10.1021/jo101799e

Cite

Citations (42)

Unlocking Access to Enantiopure Fused Uracils by Chemodivergent [4+2] Cross‐Cycloadditions: DFT‐Supported Homo‐Synergistic Organocatalytic Approach

Angewandte Chemie International Edition (2020)

Claudio Curti Gloria Rassu Marco Lombardo Vincenzo Zambrano Luigi Pinna

The discovery of chemical methods enabling the construction of carbocycle-fused uracils which embody a three-dimensional and functional-group-rich architecture is a useful tool in medicinal chemistry oriented synthesis. In this work, an unprecedented amine-catalyzed [4+2] cross-cycloaddition is documented; it involves remotely enolizable 6-methyluracil-5-carbaldehydes and β-aryl enals, and chemoselectively produces two novel bicyclic and tricyclic fused uracil chemotypes in good yields with a maximum level of enantiocontrol. In-depth mechanistic investigations and control experiments support an intriguing homo-synergistic organocatalytic approach, where the same amine organocatalyst concomitantly engages both aldehyde partners in a stepwise eliminative [4+2] cycloaddition, whose vinylogous iminium ion intermediate product may diverge-depending upon conditions-to either bicyclic targets by hydrolysis or tricyclic products by a second homo-synergistic trienamine-mediated stepwise [4+2] cycloaddition.

Enantiopure drug

Iminium

10.1002/anie.202007509

Cite

Citations (15)