title: Uncatalyzed, diastereoselective vinylogous Mukaiyama aldol reactions on aqueous media: pyrrole vs furan 2-silyloxy dienes.
abstract: 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.
authors.affiliation: Dipartimento Farmaceutico, Università degli Studi di Parma, Viale G. P. Usberti 27A, I-43124 Parma, Italy. claudio.curti@unipr.it
authors.forename: Claudio
authors.initials: C
authors.lastname: Curti
authors.forename: Lucia
authors.initials: L
authors.lastname: Battistini
authors.forename: Franca
authors.initials: F
authors.lastname: Zanardi
authors.forename: Gloria
authors.initials: G
authors.lastname: Rassu
authors.forename: Vincenzo
authors.initials: V
authors.lastname: Zambrano
authors.forename: Luigi
authors.initials: L
authors.lastname: Pinna
authors.forename: Giovanni
authors.initials: G
authors.lastname: Casiraghi
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D011758:Pyrroles; D012821:Silanes; D014867:Water