Reduction and Reductive Alkylation of α- tert -Butylthio Carbonyl Compounds. An Efficient Method for Stepwise α-Alkylation of Esters, Nitriles and Ketones Via the α- Tert -Butylthio Derivatives
1973; Taylor & Francis; Volume: 3; Issue: 4 Linguagem: Inglês
10.1080/00397917308065914
ISSN1532-2432
AutoresS. Kamata, Shoichiro Uyeo, N. HAGA, Wataru Nagata,
Tópico(s)Synthesis of heterocyclic compounds
ResumoAbstract An efficient and generally applicable method for stepwise α-alkylatton of esters, nitriles, and ketones via the α-tert-butylthio derivatives is described. The method involves reductive-protonation and reductive-alkylation of α-alkylthio α,α-bis-alkylated carbonyl compounds which are prepared by stepwise alkylation of the corresponding simple α-alkylthio carbonyl precursors. The reduction is conveniently performed by use of stoichiometric amounts of a dissolving metal, particularly lithium, affording correspondingly the α-mono-and the α,α-bis-alkylated carbonyl compounds in good yields.
Referência(s)