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Solvent‐ and Structure‐Dependent Regioselectivity in the Boron‐Mediated Aldol Reaction of 2‐(1,3‐Dioxolan‐2‐yl)ethyl Ethyl Ketones
Author(s) -
Lanners Steve,
NorouziArasi Hassan,
Khiri Naima,
Hanquet Gilles
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700320
Subject(s) - regioselectivity , chemistry , aldol reaction , ketone , diethyl ether , ether , structural isomer , solvent , stereochemistry , organic chemistry , medicinal chemistry , catalysis
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‐ring derivatives. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)