The development of enabling chemical transformations which exploit highly functionalized polydentate substrates – e.g. π-extended carbonyl compounds – with maximum efficiency and chemo-, regio-, and stereocontrol is a main challenge at the forefront of organic synthesis. To this end, merging the vinylogy concept with the malononitrile activation strategy, and the chiral iminium ion LUMO-lowering catalysis turned out to be a successful option, and several achievements were recently obtained on the exploitation of these concepts in asymmetric synthesis. We herein emphasize the role of the malononitrile handle as a crucial (and optionally traceless) ingredient enabling the selective activation of polyunsaturated carbonyl pro- nucleophiles. In particular, the synthetic potential of previously uncharted vinylogous alkylidene malononitriles I-III is highlighted, together with the modalities by which the efficient and chemo-, regio-, diastereo-, and enantioselective synthesis of collections of valuable carbocyclic and heterocyclic compounds were realized.

Exploring the Remote Reactivity of π-Extended Carbonyl Compounds: the Vinylogous Alkylidene Malononitrile Activation Strategy / Curti, Claudio; Rassu, Gloria; Battistini, Lucia; Sartori, Andrea; Brindani, Nicoletta; Zanardi, Franca. - ELETTRONICO. - (2016), pp. OC-32-OC-32. ((Intervento presentato al convegno XXXVII Convegno Nazionale della Divisione di Chimica Organica tenutosi a Mestre (VE) nel 18-22 Settembre 2016.

Exploring the Remote Reactivity of π-Extended Carbonyl Compounds: the Vinylogous Alkylidene Malononitrile Activation Strategy

CURTI, Claudio;BATTISTINI, Lucia;SARTORI, Andrea;BRINDANI, Nicoletta;ZANARDI, Franca
2016

Abstract

The development of enabling chemical transformations which exploit highly functionalized polydentate substrates – e.g. π-extended carbonyl compounds – with maximum efficiency and chemo-, regio-, and stereocontrol is a main challenge at the forefront of organic synthesis. To this end, merging the vinylogy concept with the malononitrile activation strategy, and the chiral iminium ion LUMO-lowering catalysis turned out to be a successful option, and several achievements were recently obtained on the exploitation of these concepts in asymmetric synthesis. We herein emphasize the role of the malononitrile handle as a crucial (and optionally traceless) ingredient enabling the selective activation of polyunsaturated carbonyl pro- nucleophiles. In particular, the synthetic potential of previously uncharted vinylogous alkylidene malononitriles I-III is highlighted, together with the modalities by which the efficient and chemo-, regio-, diastereo-, and enantioselective synthesis of collections of valuable carbocyclic and heterocyclic compounds were realized.
Exploring the Remote Reactivity of π-Extended Carbonyl Compounds: the Vinylogous Alkylidene Malononitrile Activation Strategy / Curti, Claudio; Rassu, Gloria; Battistini, Lucia; Sartori, Andrea; Brindani, Nicoletta; Zanardi, Franca. - ELETTRONICO. - (2016), pp. OC-32-OC-32. ((Intervento presentato al convegno XXXVII Convegno Nazionale della Divisione di Chimica Organica tenutosi a Mestre (VE) nel 18-22 Settembre 2016.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11381/2825198
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