Synthesis of N-allylideneamines and their use for the double nucleophilic addition of ketene silyl (thio)acetals and trimethylsilyl cyanide.
N-Allylideneamines 1a, b were prepared from acrolein and diphenylethyl or trityl amine in the presence of Ti(OEt)4. Double nucleophilic addition of various ketene silyl (thio)acetals and trimethylsilyl cyanide to these imines proceeded efficiently to give, after workup with TFA, homoglutamic acid derivatives 3 and valerolactam 5.
Mizota
Isao
I
Department of Chemistry for Materials, Graduate School of Engineering, Mie University, Tsu, Mie 514-8507, Japan.
Matsuda
Yuri
Y
Hachiya
Iwao
I
Shimizu
Makoto
M
D000080:Acetals / Q000737:chemistry*; D000171:Acrolein / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D003486:Cyanides / Q000737:chemistry*; D005030:Ethylenes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D012825:Silicon / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D000080:Acetals; D000588:Amines; D003486:Cyanides; D005030:Ethylenes; D007659:Ketones; D014297:Trimethylsilyl Compounds; C058010:trimethylsilyl cyanide; D000171:Acrolein; C008223:ketene; D012825:Silicon