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| - Alkylation, Aldol, and Related Reactions ofO-Alkanoyl- and 2-AlkenoylTEMPOs(2,2,6,6-Tetramethylpiperidine-N-oxyl): Insightinto the Reactivity of Their Anionic Species inComparison with Esters and Amides
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| - The lithium anionic species generated from O-alkanoylTEMPOs upon treatment with LDA were first employed as anucleophile for alkylation, Michael addition, direct aldolreaction, and others. The alkylation occurred smoothly atthe methylene carbon, and no alkylation was found in theisobutyryl analogue, while silylation was scarcely attainable.Substitutions of the heteroatom were achieved by reactionwith PhSSPh and DEAD. The reactivity of these anionicspecies is successfully extended to aldol reactions in whichmoderate anti or syn selectivity was executed with propionylderivatives. Tandem Michael addition of lithium amidefollowed by aldol reaction was performed on the O-crotonoylTEMPOs.
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