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

…, H Norouzi??Arasi, N Khiri, G Hanquet

Index: Lanners, Steve; Norouzi-Arasi, Hassan; Khiri, Naima; Hanquet, Gilles European Journal of Organic Chemistry, 2007 , # 24 p. 4065 - 4075

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Citation Number: 10

Abstract

Abstract The regioselectivity of the Chx 2 BCl/Et 3 N-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 1 H NMR studies of six-membered- ...