Organocatalyzed direct aldol condensation using L-proline and BINAM-prolinamides: regio-, diastereo-, and enantioselective controlled synthesis of 1,2-diols

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Title: Organocatalyzed direct aldol condensation using L-proline and BINAM-prolinamides: regio-, diastereo-, and enantioselective controlled synthesis of 1,2-diols
Authors: Guillena, Gabriela | Hita López, María del Carmen | Nájera, Carmen
Research Group/s: Derivados de Aminoácidos y Péptidos en Síntesis Orgánica | Procesos Catalíticos en Síntesis Orgánica
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica
Keywords: Organocatalysis | Aldol | Enantioselective | Asymmetric synthesis | Amino acids | Proline
Knowledge Area: Química Orgánica
Issue Date: 3-Apr-2006
Publisher: Elsevier
Citation: GUILLENA TOWNLEY, Gabriela; HITA, María del Carmen; NÁJERA DOMINGO, Carmen. "Organocatalyzed direct aldol condensation using L-proline and BINAM-prolinamides: regio-, diastereo-, and enantioselective controlled synthesis of 1,2-diols". Tetrahedron: Asymmetry. Vol. 17, Issue 7 (3 Apr. 2006). ISSN 0957-4166, pp. 1027-1031
Abstract: Recoverable BINAM-prolinamide derivatives, as well as L-proline, give results complementary to antibodies when used as organocatalysts for aldol eactions between aldehydes and α-alkoxyacetones driving regioselectively to anti/syn-1,2-diols. The formation of the iso-regioisomer is suppressed using α-hydroxyacetone in DMSO at rt, achieving the corresponding anti-1,2-diol with ee’s up to 85%. For α-alkoxyacetones (methoxy, benzyloxy, and tert-butyldimethylsilyloxy), the highest regio- and diastereoselectivity is achieved using α-methoxyacetone in DMF at 0 °C; the enantiomeric excess for the anti-1,2-isomer being up to 98%.
Sponsor: This work was financially supported by the Dirección General de Investigación of the Ministerio de Educación y Ciencia of Spain (Grant BQU2001-0724-CO2-01 and CTQ2004-00808/BQU), the Generalitat Valenciana (Grant CTIOIB/2002/320, GRUPOS03/134, and GV05/157) and the University of Alicante.
URI: http://hdl.handle.net/10045/2507
ISSN: 0957-4166
DOI: 10.1016/j.tetasy.2006.03.023
Language: eng
Type: info:eu-repo/semantics/article
Peer Review: si
Publisher version: http://dx.doi.org/10.1016/j.tetasy.2006.03.023
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