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Communication | Regular issue | Vol 85, No. 5, 2012, pp.1045-1052
Published online, 23rd March, 2012
DOI: 10.3987/COM-12-12442
One Step Synthesis of Optically Active Diazabicyclo[3.3.0]octanones or Diazabicyclo[4.3.0]nonanones by Asymmetric Conjugate Addition of Cyclic Hydrazine

Chigusa Seki,* Masafumi Hirama, Takeshi Sato, Saya Takeda, Yoshihito Kohari, Kazuhiro Ishigaki, Masafumi Ohuchi, Kiyoshi Yokoi, Hiroto Nakano, Koji Uwai, Nobuhiro Takano, Kazuyuki Umemura, and Haruo Matsuyama*

*Department of Applied Chemistry, Graduate School of Engineering, Muroran Institute of Technology, 27-1 Mizumoto, Muroran, Hokkaido 050-8585, Japan

Abstract

Asymmetric conjugate addition-cyclization of lithium amide of 6-membered hydrazine 4, piperidazine, (or 5-membered hydrazine 6, pyrazolidine) to N-(E)-cinnamoyl-(1S)-2,10-camphorsultam (1S)-3 afforded β-amino acid derivative (S)-1 {or (S)-2} for the synthesis of polyamine alkaloids in good yield with good stereoselectivity (up to 86% ee).