Regioselective Robinson Annulation Realized by the Combined Use of Lithium Enolates and Aluminum Tris (2, 6-diphenylphenoxide)(ATPH).

…, I Shimada, Y Takamori, M Tanaka, K Maruoka…

Index: Saito, Susumu; Shimada, Itsuro; Takamori, Yusuke; Tanaka, Michiaki; Maruoka, Keiji; Yamamoto, Hisashi Bulletin of the Chemical Society of Japan, 1997 , vol. 70, # 7 p. 1671 - 1681

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Citation Number: 8

Abstract

Michael addition of lithium enolates derived from ketones to a variety of α, β-unsaturated ketones was realized in the presence of aluminum tris (2, 6-diphenylphenoxide)(ATPH). In this reaction, ATPH can be used as a carbonyl protector of α, β-unsaturated carbonyl substrates upon complexation, which facilitates the regioselective 1, 4-addition of lithium enolates to Michael acceptors. Similarly, dianions of β-dicarbonyl compounds undergo ...