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dc.creatorPalomo, Claudioes_ES
dc.creatorOiarbide, Mikeles_ES
dc.creatorGómez Bengoa, Enriquees_ES
dc.creatorMielgo, Antoniaes_ES
dc.creatorGonzález Rego, María Concepciónes_ES
dc.creatorGarcía Castillo, Jesús Maríaes_ES
dc.creatorGonzález Guerrero, Albertoes_ES
dc.creatorOdriozola Ibarguren, José Manueles_ES
dc.creatorBañuelos, Patriciaes_ES
dc.creatorLinden, Anthonyes_ES
dc.description.abstractThe presented lithium enolate-based methodology is suitable for access to propionate syn-aldol motifs with high levels of stereocontrol. The reactive lithium enolate species is generated by direct treatment of a camphor-based chiral ethyl ketone with butyllithium, and is subsequently submitted to aldolization with a broad variety of aldehydes. The product aldols are obtained in uniformly high yields and high d.r. values (ranging from 91:9 to >98:2) irrespective of the aliphatic (both linear and branched chain), α,β-unsaturated, aromatic, or hetero-aromatic nature of the aldehyde employed. The crystallinity of most of the obtained adducts offers an easy access to almost 100% isomerically pure products upon a single recrystallisation. The auxiliary (1R)- (+)-camphor can be removed easily from the adducts for reuse, thereby producing the corresponding syn propionate aldols. This technology is implemented in the synthesis of a key subunit of the multi-drug resistance reversing agent hapalosin.en
dc.description.sponsorshipThis work was finantially supported by the Universidad del País Vasco, Gobierno Vasco, and by MEC. Grants to M. C. G.-R. from Gobierno Vasco and to P. B. from MEC are acknowledged.en
dc.format.extent16 p.
dc.publisherARKAT USA, Inc.en
dc.relation.ispartofARKIVOC 2005 (vi) 377-392en
dc.rights©ARKAT USA, Inc.en
dc.rightsCreative Commons Attribution-NonCommercial 4.0 International (CC BY-NC 4.0)en
dc.subjectLithium enolatesen
dc.subjectAldol reactionen
dc.subjectAsymmetric synthesisen
dc.titleAsymmetric propionate aldol reactions of a chiral lithium enolate accessible from direct enolization with n-butyllithiumen
dc.typeArtículo / Artikuluaes
dc.contributor.departmentQuímica Aplicadaes_ES
dc.contributor.departmentKimika Aplikatuaeu
dc.rights.accessRightsAcceso abierto / Sarbide irekiaes
dc.type.versionVersión publicada / Argitaratu den bertsioaes

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