Asymmetric propionate aldol reactions of a chiral lithium enolate accessible from direct enolization with n-butyllithium
| dc.contributor.author | Palomo, Claudio | |
| dc.contributor.author | Oiarbide, Mikel | |
| dc.contributor.author | Gómez Bengoa, Enrique | |
| dc.contributor.author | Mielgo, Antonia | |
| dc.contributor.author | González Rego, María Concepción | |
| dc.contributor.author | García Castillo, Jesús María | |
| dc.contributor.author | González Guerrero, Alberto | |
| dc.contributor.author | Odriozola Ibarguren, José Manuel | |
| dc.contributor.author | Bañuelos Villaverde, Patricia | |
| dc.contributor.author | Linden, Anthony | |
| dc.contributor.department | Química Aplicada | es_ES |
| dc.contributor.department | Kimika Aplikatua | eu |
| dc.date.accessioned | 2017-02-10T09:41:37Z | |
| dc.date.available | 2017-02-10T09:41:37Z | |
| dc.date.issued | 2005 | |
| dc.description.abstract | The 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.sponsorship | This 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.extent | 16 p. | |
| dc.format.mimetype | application/pdf | en |
| dc.identifier.issn | 1424-6376 | |
| dc.identifier.uri | https://academica-e.unavarra.es/handle/2454/23502 | |
| dc.language.iso | eng | en |
| dc.publisher | ARKAT USA, Inc. | en |
| dc.relation.ispartof | ARKIVOC 2005 (vi) 377-392 | en |
| dc.rights | ©ARKAT USA, Inc. | en |
| dc.rights | Creative Commons Attribution-NonCommercial 4.0 International (CC BY-NC 4.0) | en |
| dc.rights.accessRights | info:eu-repo/semantics/openAccess | |
| dc.rights.uri | https://creativecommons.org/licenses/by-nc/4.0/ | |
| dc.subject | Lithium enolates | en |
| dc.subject | Aldol reaction | en |
| dc.subject | Asymmetric synthesis | en |
| dc.subject | Hapalosin | en |
| dc.subject | Butyllithium | en |
| dc.title | Asymmetric propionate aldol reactions of a chiral lithium enolate accessible from direct enolization with n-butyllithium | en |
| dc.type | info:eu-repo/semantics/article | |
| dc.type.version | info:eu-repo/semantics/publishedVersion | |
| dspace.entity.type | Publication | |
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