Synthesis of (±)-angustione by the regioselective alkylation of enaminodiketones under the action of strong bases

Zenyuk, A. A.; Korchuk, A. V.; Ukhova, L. I.; Lis, L. G.

doi:10.1007/bf00601277

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Chemical Properties Of Vinylogous Amides2

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1999

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“…A procedure for the regioselective C-alkylation of cyclohexane β-triketone enamino derivatives in the presence of strong bases has been proposed . Pyrrolidine enamines ( 158, 159 ) can be alkylated at the α-position by LDA and methyl iodide in THF yielding 80% and 65% of the ring-methylated products ( 160, 161 ), respectively (Scheme ).…”

Section: Chemical Properties Of Vinylogous Amidesmentioning

confidence: 99%

“…103 A procedure for the regioselective C-alkylation of cyclohexane β-triketone enamino derivatives in the presence of strong bases has been proposed. 105 Pyrrolidine enamines (158, 159) can be alkylated at the R-position by LDA and methyl iodide in THF yielding 80% and 65% of the ring-methylated products (160, 161), respectively (Scheme 34). The use of lithium bis(trimethylsilyl)amide as a base permits the methylation of the enamine (158) to be directed toward the acyl chain with the exclusive formation of the γ-methylated enamino diketone (162).…”

Section: Chemical Properties Of Vinylogous Amidesmentioning

confidence: 99%

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