SN2' alkylation of chiral allylic cyanohydrin o-phosphates with organocuprates
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Campo DC | Valor | Idioma |
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dc.contributor | Procesos Catalíticos en Síntesis Orgánica | en |
dc.contributor.author | Baeza, Alejandro | - |
dc.contributor.author | Nájera, Carmen | - |
dc.contributor.author | Sansano, Jose M. | - |
dc.contributor.other | Universidad de Alicante. Departamento de Química Orgánica | en |
dc.date.accessioned | 2007-11-02T07:52:59Z | - |
dc.date.available | 2007-11-02T07:52:59Z | - |
dc.date.issued | 2007-01-08 | - |
dc.identifier.citation | BAEZA CARRATALÁ, Alejandro; NÁJERA DOMINGO, Carmen; SANSANO GIL, José Miguel. "SN2' alkylation of chiral allylic cyanohydrin o-phosphates with organocuprates". European Journal of Organic Chemistry. Vol. 2007, Issue 7. ISSN 1434-193X, pp. 1101-1112 | en |
dc.identifier.issn | 1434-193X | - |
dc.identifier.uri | http://hdl.handle.net/10045/2685 | - |
dc.description.abstract | Enantiomerically enriched cyanohydrin O-phosphates, prepared by enantioselective cyanophosphorylation of α,β-unsaturated aldehydes, react regioselectively at the γ-position with organocuprates derived from alkyl Grignard reagents and CuCN to afford chiral γ-alkyl-substituted α,β-unsaturated nitriles. The configuration of the new C–C double bond is mainly (E) when the reaction is performed at –78 °C and (Z) when it is carried out at higher temperatures (0 °C). A high level of transfer of the chirality in the new stereocentre, corresponding to a stereospecific anti attack onto the cyanophosphate, is observed. Enantiomerically enriched (E)-γ-alkylated α,β-unsaturated esters are prepared after subsequent methanolysis in a three-step sequence from the corresponding α,β-unsaturated aldehydes. In addition, the synthesis of (R)-4-methylnonan-1-ol, also known as the sex pheromone of the yellow mealworm Tenebrio molitor L, and its (S) enantiomer have been carried out in a four-step route from (E)-oct-2-enal. | en |
dc.description.sponsorship | This work has been supported by the DGES of the Spanish Ministerio de Educación y Ciencia (MEC) (CTQ2004-00808/BQU), the Generalitat Valenciana (CTIOIB/2002/320, GRUPOS03/134 and GV05/144) and the University of Alicante. | en |
dc.language | eng | en |
dc.publisher | Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim | en |
dc.subject | Cyanohydrins | en |
dc.subject | Organocuprates | en |
dc.subject | Copper | en |
dc.subject | Allylic substitution | en |
dc.subject | Asymmetric synthesis | en |
dc.subject | Unsaturated nitriles | en |
dc.subject | Cyanophosphates | en |
dc.subject.other | Química Orgánica | en |
dc.title | SN2' alkylation of chiral allylic cyanohydrin o-phosphates with organocuprates | en |
dc.type | info:eu-repo/semantics/article | en |
dc.peerreviewed | si | en |
dc.identifier.doi | 10.1002/ejoc.200600822 | - |
dc.relation.publisherversion | http://dx.doi.org/10.1002/ejoc.200600822 | - |
dc.rights.accessRights | info:eu-repo/semantics/restrictedAccess | - |
Aparece en las colecciones: | INV - PCSO - Artículos de Revistas INV - SINTAS - Artículos de Revistas INV - CESO - Artículos de Revistas INV - AMIC - Artículos de Revistas |
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