Solvent- and Structure-Dependent Regioselectivity in the Boron-Mediated Aldol Reaction of 2-(1,3-Dioxolan-2-yl)ethyl Ethyl Ketones

Solvent- and Structure-Dependent Regioselectivity in the Boron-Mediated Aldol Reaction of 2-(1,3-Dioxolan-2-yl)ethyl Ethyl Ketones

The regioselectivity of the Chx2BCl/Et3N‐mediated (Chx = cyclohexyl) aldol reactions of ketones of general structure 2 has been studied and was shown to depend on both ketone structure and solvent. Useful levels of regioselectivity in favour of any of the two possible regioisomers were obtained in e...

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Veröffentlicht in:European Journal of Organic Chemistry 2007-08, Vol.2007 (24), p.4065-4075
Hauptverfasser: Lanners, Steve, Norouzi-Arasi, Hassan, Khiri, Naima, Hanquet, Gilles
Format: Artikel
Sprache:eng
Schlagworte:
Aldol reactions
Boron
Ketones
Regioselectivity
Solvent effects
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Beschreibung
Zusammenfassung:The regioselectivity of the Chx2BCl/Et3N‐mediated (Chx = cyclohexyl) aldol reactions of ketones of general structure 2 has been studied and was shown to depend on both ketone structure and solvent. Useful levels of regioselectivity in favour of any of the two possible regioisomers were obtained in either pentane or diethyl ether. The relative configuration of the aldol products was assigned by 1H NMR studies of six‐membered‐ring derivatives. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200700320