4,4-Dimethyl-2-(3-chloro-2-methyl-l-propenyl)-2-oxazoline has been synthesized and deprotonated with LDA in THF to give the corresponding lithiated species, which has been found to react alpha-regioselectively with NH4Cl and alkyl halides, and y-regioselectively with carbonyl compounds to afford alpha-protonated (or cc-alkyl-substituted) regioisomers and vinyl epoxides, respectively. The Z diastereoselectivity of both the protonation and the allcylation reactions was usually found to increase with the temperature. Ab initio calculations, performed on both the naked lithium salt and the corresponding solvated form, support the observed regioselectivity. (C) 2015 Elsevier Ltd. All rights reserved.
Regio- and stereochemical aspects in the functionalisation of a lithiated 2-(3-chloro-2-methyl-1-propenyl)-2-oxazoline: electrophile and temperature effects
Rocchetti, MT;
2015-01-01
Abstract
4,4-Dimethyl-2-(3-chloro-2-methyl-l-propenyl)-2-oxazoline has been synthesized and deprotonated with LDA in THF to give the corresponding lithiated species, which has been found to react alpha-regioselectively with NH4Cl and alkyl halides, and y-regioselectively with carbonyl compounds to afford alpha-protonated (or cc-alkyl-substituted) regioisomers and vinyl epoxides, respectively. The Z diastereoselectivity of both the protonation and the allcylation reactions was usually found to increase with the temperature. Ab initio calculations, performed on both the naked lithium salt and the corresponding solvated form, support the observed regioselectivity. (C) 2015 Elsevier Ltd. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
