Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

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

Abstract

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.