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Exploring the boundaries of vinylogous Mukaiyama aldol processes: stereoselective access to polyunsaturated homoallylic alcohols

Curti, Claudio and Rassu, Gloria Maria Rita and Sartori, Andrea and Battistini, Lucia and Zanardi, Franca (2013) Exploring the boundaries of vinylogous Mukaiyama aldol processes: stereoselective access to polyunsaturated homoallylic alcohols. In: 35. Convegno della Divisione di chimica organica della Società Chimica Italiana, 9-13 settembre 2013, Sassari, Italia. [S.l.], Società Chimica Italiana, Divisione di chimica organica. O4. Conference or Workshop Item.

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Abstract

Catalytic enantioselective vinylogous aldol reactions using extended enolates are of prominent value in synthetic organic chemistry. Here, we report our advances in the development of enantioselective bis-vinylogous and hyper-vinylogous Mukaiyama aldol reactions between a series of polyenylsilyloxy furans or polyenylsilyoxy indoles and aromatic aldehydes, realized by use of the enabling catalyst combination of silicon tetrachloride and Denmark’s chiral bis-phosphoramide base (R,R)-I. Several crucial issues such as the remote site-, enantio- and geometrical selectivity of the reaction will be highlighted, ultimately focusing on one main question: how far can we push the limits of the vinylogous reactivity transmittal?

Item Type:Conference or Workshop Item (Lecture)
ID Code:9281
Status:Published
Uncontrolled Keywords:Synthetic organic chemistry, enantioselective bis-vinylogous reaction, hyper-vinylogous Mukaiyama aldol reaction
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:Società Chimica Italiana, Divisione di chimica organica
Publisher Policy:Depositato per gentile concessione dell'Editore
Deposited On:04 Nov 2013 13:38

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