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Catalytic, asymmetric hypervinylogous Mukaiyama aldol reactions of extended furan-based silyl enolates

Curti, Claudio and Battistini, Lucia and Sartori, Andrea and Lodola, Alessio and Mor, Marco and Rassu, Gloria Maria Rita and Pelosi, Giorgio and Zanardi, Franca and Casiraghi, Giovanni (2011) Catalytic, asymmetric hypervinylogous Mukaiyama aldol reactions of extended furan-based silyl enolates. Organic Letters, Vol. 13 (17), p. 4738-4741. ISSN 1523-7060. eISSN 1523-7052. Article.

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DOI: 10.1021/ol2020626

Abstract

Virtually perfect transmittal of the enolate reactivity up to five conjugated double bonds from the origin allows a series of furan-based silyloxypolyenes to add to aldehyde carbonyls at the most distant point of the molecule. Denmark’s axially chiral bisphosphoramide/SiCl4 combination catalyzes these scantly precedented, long-range Mukaiyama-type vinylogous aldol reactions efficiently, providing a palette of extended γ-alkylidene butenolide carbinols with complete ω-site selectivity and good to excellent levels of enantioselectivity.

Item Type:Article
ID Code:6413
Status:Published
Refereed:Yes
Uncontrolled Keywords:Asymmetric catalysis, asymmetric synthesis, diastereoselectivity, enantioselectivity, heterocyclic dienoxy silanes, vinylogous 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:American Chemical Society
ISSN:1523-7060
eISSN:1523-7052
Copyright Holders:© 2011 American Chemical Society
Deposited On:26 Aug 2011 12:55

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