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Paper | Special issue | Vol 52, No. 3, 2000, pp.1143-1162
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S113
Mannich Type Reactions of Acylhydrazones with Silyl Enolates for the Synthesis of β-Amino Ester, β-Amino Ketone, β-Lactam, Pyrazolidinone, and Pyrazolone Derivatives

Osamu Okitsu, Hidekazu Oyamada, Takayuki Furuta, and Shu Kobayashi*

*Graduate School of Pharmaceutical Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan


In the presence of a catalytic amount of a rare earth triflate, acylhydrazones reacted with silyl enolates to afford the corresponding β-N'-acylhydrazino esters in high yields. A three-component reaction of an aldehyde, an acyihydrazine, and a silyl enolate was also performed successfully. The hydrazino esters thus obtained were readily converted to β-amino ester, β-amino ketone, β-lactam, pyrazolidinone, and pyrazolinone derivatives.