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Communication | Regular issue | Vol 24, No. 10, 1986, pp.2785-2789
Published online, 1st January, 1970
DOI: 10.3987/R-1986-10-2785
Tandem Reductive Amination and Michael Addition. Synthesis of Optically Active Pyrrolidine Nucleus

Seiki Saito, Shingo Matsumoto, Shuji Sato, Masami Inaba, and Toshio Moriwake*

*Department of Applied Chemistry, Faculty of Engineering, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan


Reductive amination of ethyl (E)-(4S)-4-methoxymethoxy-6-oxo-2-hexenoate, derived from (S)-malic acid, with glycine ethyl ester was relayed intramolecularly by Michael-type addition, which has led, in one pot, to N-substituted (2R,3S)-2-ethoxycarbonylmethyl-3-hydroxypyrrolidine skeleton, a promising precursor for optically active necine bases such as (+)-heliotridine.