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Por favor, use este identificador para citar o enlazar este ítem: http://uvadoc.uva.es/handle/10324/21449
Título: Tandem Diastereo- and Enantioselective Preparation of Aryl and Alkyl Cyclopropyl Carbinols with Three Adjacent Stereocenters Using Perhydrobenzoxazines and Diethylzinc
Autor: Infante Blanco, Rebeca
Nieto Román, Francisco Javier
Andrés Juan, Celia
Año del Documento: 2014
Editorial: Royal Society of Chemistry
Descripción: Producción Científica
Documento Fuente: Organic & Biomolecular Chemistry, 2014, 12, p. 345-354
Resumen: The enantio‐ and diastereoselective one‐pot ethylation/cyclopropanation is efficiently promoted by a chiral perhydrobenzoxazine. The catalytic system tolerates a wide range of di‐ and trisubstituted α,β‐unsaturated aldehydes and has been found to be highly diastereo- and enantioselective. Enals leading to intermediates lacking allylic strain or with either A1,2 or A1,3 strain afford the corresponding syn hydroxycyclopropanes very selectively. While α‐methyl enals are successfully ethylated/cyclopropanated, the presence of bulky substituents at alpha position of the enal constitutes a limitation to the substrate scope. The use of 1,1‐diiodoethane allows the obtention of the corresponding enantioenriched cyclopropylcarbinol, which bears carbon‐substituents at all three positions of the ring, with good enantiocontrol, although moderate diastereoselectivity. A procedure for the asymmetric one‐pot arylation/cyclopropanation of enals is proposed, which involves the use of triarylboroxin, diethylzinc and diiodomethane.
Materias (normalizadas): Química orgánica
ISSN: 1477-0520
Revisión por Pares: SI
DOI: 10.1039/C3OB41797B
Patrocinador: Ministerio de Economía, Industria y Competitividad (CTQ 2011-28487)
Junta de Castilla y León (programa de apoyo a proyectos de investigación – Ref. VA064U13)
Universidad de Valladolid for a pre-doctoral fellowships
Version del Editor: http://pubs.rsc.org/
Idioma: eng
URI: http://uvadoc.uva.es/handle/10324/21449
Derechos: info:eu-repo/semantics/openAccess
Aparece en las colecciones:DEP67 - Artículos de revista

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