Deprotonation of β, β-disubstituted α, β-unsaturated amides-Mechanism and stereochemical consequences

…, M Majewski, V Snieckus

Index: Green, James R.; Majewski, Marek; Snieckus, Victor Canadian Journal of Chemistry, 2006 , vol. 84, # 10 p. 1397 - 1410

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Citation Number: 4

Abstract

A detailed study of the lithium dialkylamide induced deprotonation of β, β-disubstituted α, β- unsaturated amides is presented. The preferential γ-Z-deprotonation and stereochemical outcome of substituents on the γ-Z carbon atom are rationalized in terms of a cyclic eight- membered transition state, which is supported by DFT calculations. Analogous deprotonations on cyclohexylidenecarboxamides reveal a delicate balance of the ...