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Reactions of lithium enolates with molecular oxygen α-hydroxylation of amides and other carboxylate derivatives

✍ Scribed by Harry H. Wasserman; Bruce H. Lipshutz

Book ID
104213745
Publisher
Elsevier Science
Year
1975
Tongue
French
Weight
215 KB
Volume
16
Category
Article
ISSN
0040-4039

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✦ Synopsis

Recently, lithium diisopropylamide (LDA) and related hindered bases have found widespread use in the formation of enolate anions of acids, esters, and other carboxylate derivatives. In suitable solvents such as TRF and RMPA at low temperatures, these anions have been employed in a variety of reactions including alkylation, 1 acylation, 2 halogenation, 3 sulfenylation, 4 selenenylation, 5 and amination. 6 The methods have been notable for their mildness, specificity, good yields and absence of side reactions such as self-condensation.

We now report that carbanions generated in the reactions of N,N-dialkyl a&ides with alkyllithium reagents undergo rapid oxidation under mild conditions when treated with molecular oxygen, Recently, the reactions of oxygen with secondary nitrile anions generated by LDA have led to cyanohydrins, and subsequently, to ketones in good yields (S.

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