Selectivity in. beta.-enamino ketone anion generation and alkylation

YL Chen, PS Mariano, GM Little, D O'Brien…

Index: Chen, Yuhpyng Liang; Mariano, Patrick S.; Little, Garrick M.; O'Brien, Daniel; Huesmann, Peter L. Journal of Organic Chemistry, 1981 , vol. 46, # 23 p. 4643 - 4654

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Citation Number: 49

Abstract

The regioselectivity of anion generation from@-alkoxy-and@-(dialkylamino)-a, B-uaturated ketones was probed by use of 13C NMR spectroscopy and alkylation techniques. Results indicate that the kinetic anions of these systems can be formed selectively from the parent ketones by using excess lithium diisopropylamide as the base at-78 OC and diethyl ether or tetrahydrofuran as the solvent. The kinetic anion in these systems is the one resulting from ...