title: Catalytic, asymmetric hypervinylogous Mukaiyama aldol reactions of extended furan-based silyl enolates.
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/SiCl(4) 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.
authors.affiliation: Dipartimento Farmaceutico, Università degli Studi di Parma, Parco Area delle Scienze 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: Andrea
authors.initials: A
authors.lastname: Sartori
authors.forename: Alessio
authors.initials: A
authors.lastname: Lodola
authors.forename: Marco
authors.initials: M
authors.lastname: Mor
authors.forename: Gloria
authors.initials: G
authors.lastname: Rassu
authors.forename: Giorgio
authors.initials: G
authors.lastname: Pelosi
authors.forename: Franca
authors.initials: F
authors.lastname: Zanardi
authors.forename: Giovanni
authors.initials: G
authors.lastname: Casiraghi
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D015394:Molecular Structure; D063088:Phosphoramides; D010756:Phosphoric Acids / Q000737:chemistry*; D017655:Silicon Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000447:Aldehydes; D000577:Amides; D002712:Chlorides; D005663:Furans; D063088:Phosphoramides; D010756:Phosphoric Acids; D017655:Silicon Compounds; C005438:phosphoramide; C039676:silicon tetrachloride; C039281:furan